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Holiday Rentals near Portland Castle

Portland Castle Liberty Road, Castletown, DT5 1AZ, England
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    Travellers to Isle of Portland are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    All 100 Rentals in Isle of Portland
    65 Fortuneswell - 180° Sea Views from Balcony1 / 19
    (38)Excellent
    0.9 kilometres from Portland Castle
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Fishermans Cottage1 / 42
    (26)Very good
    4.1 kilometres from Portland Castle
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Quarries Reach, rural & sea views Portland, Dorset1 / 17
    (57)Excellent
    3.9 kilometres from Portland Castle
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Traditional Welcoming Stone Farmhouse - Smugglers Haunt, Weymouth1 / 20
    (21)Very good
    3.6 kilometres from Portland Castle
    6 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Grill
    • Central Heating
    • Wi-Fi
    • Washer
    • Patio
    • Parking
    • DVD Player
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 April 2018
    Warm & friendly welcome from Becky. We had a great holiday & would not hesitate to return here again. Lots of space for all of us.Well situated for everything we needed...
    Reviewed 19 October 2017
    The house was functional and the large number of bedrooms were beneficial. It was cosy with plenty of glasses, crockery etc. It was in a brilliant position for our long walks...
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    About this property
    Smugglers Haunt is a detached grey stoned, characteristic farmhouse in Wyke Regis, part of bustling Weymouth. The property offers guests a comfortable stay with a contemporary feel, it is very well equipped providing a real 'home from home'. It has stand out appeal with views of the Fleet, its own...
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    Weymouth, Dorset
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 10
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    Castle Cove View: private access to sandy beach1 / 19
    (24)Excellent
    3.4 kilometres from Portland Castle
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Patio
    • Central Heating
    • Ocean Views
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    Quiet part of Dorset, great walking, dog friendly and area very accommodating, walk into Weymouth in just 20 mins and see all the lively bars and some have live music but house...
    Reviewed 3 weeks ago
    A very pleasent week spent with family. Lovely weather, a clean and well equiped 3 bed property, short walk to central Weymouth and private access to a Jurasic coast beach. All...
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    About this property
    With sea views towards Portland and private access to sandy Castle Cove beach, Castle Cove View provides high quality modern accommodation perfect for family holidays or romantic getaways.  A downstairs shower room (including WC and basin) is ideal for washing down sandy children with a separate...
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    Weymouth, Dorset
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Hector our Family Holiday Cottage in Weymouth1 / 10
    (20)Excellent
    4.1 kilometres from Portland Castle
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • Secure Parking
    • Wi-Fi
    • Central Heating
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 July 2018
    We loved our stay at the Mews Cottage, great location, lovely little property. Having milk and biscuits left for our arrival was a nice touch.Having somewhere private to leave...
    Reviewed 24 May 2018
    A lovely home, convenient for the town and beach. Secure parking, with a lovely coastal walk on the doorstep, and close to all the amenities of Weymouth. From the moment you...
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    About this property
    Welcome to Hector is our family friendly luxury self catering self catering holiday cottage. Hector is located in a private gated mews behind Brewers Quay very near to the Weymouth harbour side and only a few minutes from the beach, making it ideal for walking to a local restaurant or around the...
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    Weymouth, Dorset
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    1 The Old Police Station1 / 17
    (9)Excellent
    0.5 kilometres from Portland Castle
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Private Garden
    • Wi-Fi
    • Ocean Views
    • Grill
    • DVD Player
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 July 2018
    We stayed here with our daughter and her children. It's rather amusing staying in a police station. It's convenient, a good location and it has been sympathetically converted...
    Reviewed 19 July 2018
    Well serviced and provisioned property. Tastefully decorated throughout. Funky architecture and layout adds to the experience. Location great for exploring the Jurassic Coast.
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    About this property
    A beautifully presented character house with views over Chesil Beach and Portland Harbour. This holiday home has many character features and really is a home from home. The property has a single parking space, there is also ample on road parking and a covered 'alfresco dining' seating area. A...
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    Isle of Portland, Dorset
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    Moonfleet Holiday Cottage1 / 15
    (49)Very good
    2.6 kilometres from Portland Castle
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Central Heating
    • Washer
    • Grill
    • Ocean Views
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Good location by Chesil Beach and close to Rodwell Trail. Lots to to do close by. House has everything you could need, was good for husband myself and 2 children.
    Reviewed 3 August 2018
    The house was great and had all the amenities you would wish for. The location was ideal for visiting Weymouth and Portland. Highlights of our stay were the beautiful Weymouth...
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    About this property
    Moonfleet is a two bedroom cottage located on the edge of Portland Harbour; the waters that hosted the 2012 Olmpic Sailing. Presented to a high standard this accommodation sleeps 5, with two double bedrooms (one with a double and single bed) a spacious lounge/diner and a newly landscaped garden....
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    Weymouth, Dorset
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Tides1 / 25
    (48)Excellent
    4.0 kilometres from Portland Castle
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • DVD Player
    • Parking
    • Private Garden
    • Wi-Fi
    • Central Heating
    • Ocean Views
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Perfect location with a beautiful view just steps away and a short walk to the harbour. A very well presented and equipped house.Thank you.
    Reviewed 3 weeks ago
    Tides is a fantastic property in a perfect location. So close to the beach and harbour and town that we walked everywhere. The facilities are great and there isn't anything I...
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    About this property
    Tides is a modern well appointed property located at the end of a quiet cul-de-sac and has the advantage of overlooking the picturesque bay and sailing venue used for the 2012 Olympic Games. The house is situated at the beginning of the wonderful promenade that winds around Newtons Cove and on...
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    Weymouth, Dorset
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    Pebble View1 / 9
    (20)Very good
    0.7 kilometres from Portland Castle
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Private Garden
    • Central Heating
    • DVD Player
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 August 2018
    Beautiful cottage. Well equipped little place. Was easy to find. Views from bedrooms were stunning. Was very cosy and quiet. Absolutely loved our stay here. Would definitely go...
    Reviewed 18 August 2017
    Had a great family holiday staying here. Was quiet and relaxing very friendly people found everything that we needed in pebble view fab views from the upstairs rooms plenty of...
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    About this property
    Pebbles view is a Victorian Portland stone built mid terrace cottage in the village of Fortuneswell Portland offering stunning panoramic sea views of the Jurassic coasts Chesil beach from all floors The newly refurbished cottage arranged over three floors comprises of the lounge with wooden...
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    Location Information
    Isle of Portland, Dorset
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    4.9 kilometres from Portland Castle
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Shared Indoor Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    On arrival to our holiday home at Littlesea Holiday Park you will enter a large modern kitchen/diner. A integrated fridge/freezer stands next to a boiler cupboard where you can hang your coats etc. The kitchen has a full size gas cooker, microwave, kettle, toaster etc. The living area has a large...
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    Weymouth, Dorset
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Ocean Apartment, 4 Bed, sleeps 10, 50 yds Beach, Grade II, Esplanade view. WIFI.1 / 15
    (1)Excellent
    4.9 kilometres from Portland Castle
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Ocean Views
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    Came here all the way from America with family. Slept everyone extremely comfortable! Location was lovely, so close to anything and everything. It’s the perfect spot to people...
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    About this property
    Ocean Apartment is a Grade II listed building, it dates back to the 1700’s. It has bags of old charm and character, but tastefully renovated into a superb 4 bedroomed apartment situated right in the middle of the town centre and just 50 yards from the beach. The property is deceptively huge, and...
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    Weymouth, Dorset
    Condo/Apartment - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Blue Bay Cottage - Beautiful Cottage near the harbour1 / 37
    (3)Excellent
    4.2 kilometres from Portland Castle
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Excellent cottage, fantastic location and lovely inside had everything we needed to make our stay wonderful, would recommend to anyone wanting to stay in weymouth
    Reviewed 3 weeks ago
    Beautifully presented holiday cottage in a great location. Lots of personal and luxurious touches made the stay a very comfortable one including great quality sheets and towels...
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    About this property
    Beautiful cottage with Harbour views situated in a conservation area. This recently updated cottage has a relaxing feel and is located alongside the picturesque harbour with many restaurants and cafes nearby. The kitchen is well equipped and has a dishwasher, microwave and Neff hide and slide...
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    Weymouth, Dorset
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    Marina Bay View Apartment - Portland Harbour1 / 18
    (2)Excellent
    0.1 kilometres from Portland Castle
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Indoor Pool
    • Balcony
    • Parking
    • Sauna
    • Hot Tub
    • Wi-Fi
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 December 2016
    Easy booking process. Estate agents very friendly and answered all questions quickly.Directions to the apartment and getting the keys made the checkin process easy.Apartment...
    Reviewed 30 August 2016
    My husband and I stayed here for a week in August with a five year old and a 21 month old. The apartment was very clean and had great facilities. The kitchen had almost...
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    About this property
    Marina View Apartment is a stunning modern apartment located overlooking Portland Marina and Harbour on the Isle of Portland, Dorset. The modern accommodation on two floors is well presented and offers three spacious bedrooms. Use of indoor pool and great as a base for water sports or fishing....
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    Isle of Portland, Dorset
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Rosa Cottage1 / 30
    (34)Very good
    1.0 kilometres from Portland Castle
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Balcony
    • Wi-Fi
    • Washer
    • DVD Player
    • Central Heating
    • Terrace
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 February 2018
    As soon as you walk through the door of Rosa Cottage you are greeted by its warm and pleasant atmosphere and your suprised by its size it's clean tidy and has all that you need...
    Reviewed 1 January 2018
    My family stayed here over Xmas. I had been advised that it had been nicely festively decorated. The result a fiberoptic Christmas tree and a few small objects. Which was...
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    About this property
    A beautiful restored Victorian terraced cottage, on a quiet street in the village of Fortuneswell on the Isle of Portland, only 5 minutes walk from the famous Chesil Beach and part of Dorset's glorious Jurassic Coast. 5 min drive from National Sailing Academy. This former bakery has been lovingly...
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    Location Information
    Isle of Portland, Dorset
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    Portland Hideaway1 / 8
    (10)Very good
    4.2 kilometres from Portland Castle
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Washer
    • Parking
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 August 2017
    Comfortable and surprisingly spacious, kitchen adequately equipped, owners next door but very low profile.The Hideaway is a conservatory and therefore does get very warm...
    Reviewed 24 August 2017
    Great little place. good location everywhere within easy reach. Bus stop outside house so no need to use the car. Great place for a birder to stay.
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    About this property
    The Portland Hideaway is a 4* self contained self catering unit with open plan living space.It benefits from a fully equipped kitchen,separate shower room with wc & sink,open plan bedroom/lounge area with ample seating on the reclining leather sofa's & air conditioning unit for your comfort....
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    Location Information
    Isle of Portland, Dorset
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    5 Cove Park1 / 14
    (3)Very good
    3.4 kilometres from Portland Castle
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • DVD Player
    • Central Heating
    • Ocean Views
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 December 2017
    Just leaving Portland after having a smashing Christmas and break at this delightful bungalow. It was just perfect for myself and my mum. So warm and cosy and very well equipped...
    Reviewed 30 June 2017
    Had a great stay in this lovely bungalow. Lots of home comforts and the kitchen was well equipped.Home from home. Loved the view from the veranda and the dogs enjoyed the garden.
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    About this property
    PET Friendly! A two-bedroom bungalow set in a unique coastal park offering total relaxation and fantastic sea views. The site is ideal for a place to rest your head after a day on the water or if you are looking for a relaxing quiet break by the sea. This holiday home features all the essentials...
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    Location Information
    Isle of Portland, Dorset
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Ocean House 80 yds from beach 4 Bed, 4 Bath, 4star1 / 21
    (6)Very good
    4.5 kilometres from Portland Castle
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Waterfront
    • Outdoor Dining Area
    • Washer
    • Central Heating
    • Cable/satellite TV
    • DVD Player
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 September 2017
    House was situated close to sea front, shops and harbour. Unfortunately it was also easily accessible by the nightly drunks who wondered up and down at all times of the night...
    Reviewed 11 October 2016
    This was my 2nd stay in Ocean House, and I still stand by my 1st review of this house... it's so homely and comfortable. It's been a full year sincel I was last there and it's...
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    About this property
    Ocean House is a 4 bedroom town house situated in the heart of the seaside town of Weymouth. The property has just been totally renovated throughout. The property has a wifi throughout, with all rooms having SMART TV's, full sky package. On the ground floor the property has Lounge, dining room,...
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    Weymouth, Dorset
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    Weymouth Family Caravan 2018 Prestige Bordeaux1 / 23
    (15)Excellent
    4.8 kilometres from Portland Castle
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Shared Indoor Pool
    • Ocean Views
    • Grill
    • Patio
    • Wi-Fi
    • DVD Player
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 March 2018
    We stayed in Marian's brand new 2018 caravan in Woodlands. What a stunning caravan! Very well equipped. Marian's hospitality was lovely. Caravan was equipped with towels, tea...
    Reviewed 15 August 2017
    We were absolutely delighted to arrive at such a beautifully clean, homely caravan. The welcome pack left for us was a really lovely gesture. The caravan was so well equipped it...
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    About this property
    Our brand new Swift Bordeaux prestige caravan sleeps 6 to a high degree of luxury, it is double glazed and centrally heated so why not stay for early or late season breaks as well as that restful time during the summer. Located with amazing views over Chesil Beach and Lyme Bay to east Devon. Free...
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    Chickerell, Weymouth
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Dory Cottage1 / 20
    (2)Very good
    0.9 kilometres from Portland Castle
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Private Garden
    • Patio
    • Ocean Views
    • Wi-Fi
    • Washer
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 July 2018
    My stay was with my family and cottage supplied all required, iron, hair dryer etc. Was easy to get to local shops, beach. The only thing there was no notes how to get rid of...
    Reviewed 27 February 2016
    Just come back from a few days based at this georgeous little cottage. So well placed for exploring the Dorset coast , westwards along Chesil beach over to the Jurassic coast...
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    About this property
    Three bedroom Portland Stone cottage over three floors with fabulous views over Chesil Beach and The Fleet. Just a short walk from Chesil Beach. Divers, sailors, walkers and families will love this cottage. WiFi and TV included but you will be busy watching the sunset! Three bedroom cottage...
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    Location Information
    Isle of Portland, Dorset
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    3.5 kilometres from Portland Castle
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Grill
    • Central Heating
    • Washer
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Jurassic Apartments Self Catering Holiday Home at Martleaves Farm is set in 35 acres of land of special scientific interest on the world famous Jurassic Coast in Dorset. The Holiday Home is a ground and first floor floor annex with 3 en suite bedrooms and a small private garden. On the ground...
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    Location Information
    Weymouth, Dorset
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Ted's House1 / 11
    (1)Very good
    0.7 kilometres from Portland Castle
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Central Heating
    • Wi-Fi
    • Patio
    • Washer
    • Private Garden
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 June 2018
    Just arrived home after staying for the Whitsun Week at Teds House and enjoyed our stay very much. Chesil Beach just down the road and 4 local pubs within walking distance, we...
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    About this property
    This lovely holiday home sits in the heart of Fortuneswell, Portland a short stroll from the Jurassic Coast. Sea views can be seen from the property where in the evening the rear windows provide lovely sunset viewing. The owners of the property have made this holiday property a home and offers...
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    Isle of Portland, Dorset
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Pebble Reef1 / 21
    (22)Excellent
    3.1 kilometres from Portland Castle
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Balcony
    • DVD Player
    • Grill
    • Central Heating
    • Wi-Fi
    • Terrace
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 July 2018
    Pebble Reef cottage met all our expectations. It is a short walk to the shopping area of Easton and also a short walk to Church Ope Cove. We took our two elderely mums with us...
    Reviewed 23 February 2018
    A beautiful cottage with all the amenities. The location was just perfect within walking distance to Church Ope Cove. Looks very small from the outside but amazingly big inside...
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    About this property
    Pebble Reef is a traditional Quarryman's Cottage, full of character but lovingly renovated to include all the modern comforts you need. The cottage sleeps up to six people in 3 comfortable bedrooms. Upstairs there's one double with en-suite shower room, a twin bedroom, and on the ground floor...
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    Location Information
    Isle of Portland, Dorset
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    BEAUTIFUL STUDIO APARTMENT - OCEAN VIEWS,PORTLAND1 / 31
    (33)Very good
    4.3 kilometres from Portland Castle
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • DVD Player
    • Wi-Fi
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    Have just returned from a lovely few days ,staying in this very comfortable and clean apartment , beds comfortable ,good roomy bathroom ,the views were lovely ,seemed strange to...
    Reviewed 4 weeks ago
    If you want a nice relaxing holiday,stay in oceon view apartment,we found everything clean and comfortable and a wonderfull view from the window.if you are a walker there are...
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    About this property
    A VERY MODERN HOLIDAY LET STUDIO APARTMENT LOCATED IN A QUIET POSITION ON THE ISLE OF PORTLAND NEAR WEYMOUTH IN THE HEART OF DORSET, ON THE COAST OF SOUTH WEST ENGLAND. SUITABLE FOR SINGLE OR DOUBLE OCCUPANCY. FACILITIES INCLUDE FLAT SCREEN TV, DVD PLAYER, MICROWAVE, FRIDGE, ELECTRIC KETTLE,...
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    Location Information
    Isle of Portland, Dorset
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Little Gem - Lovely Sea views1 / 19
    (36)Excellent
    3.2 kilometres from Portland Castle
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Housekeeping Included
    • Central Heating
    • Washer
    • Wi-Fi
    • Patio
    • Ocean Views
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    This rental very much lives up to its name.We enjoyed reading and relaxing on the deck or in the gazebo.The garden is pretty and well tended.The view on a clear day over to...
    Reviewed 11 August 2018
    Lovely comfortable flat with a fantastic view no issues at all, close enough to walk to Weymouth along the rodwell trail and approx £5 back in a taxi . Weymouth rib charter is...
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    About this property
    Little Gem - uninterruptable front line sea views positioned only 30 meters from sea and overlooking Portland Harbour the 2012 Olympic venue, and the remains of Sandsfoot castle. Off road dedicated parking within property boundary. Quite and tranquil location and only a 2 min walk to private sandy...
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    Weymouth, Dorset
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Artist Cottage - Charming coastal cottage on Portland :-)1 / 12
    (4)Very good
    0.8 kilometres from Portland Castle
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Terrace
    • Shared Garden
    • Balcony
    • Ocean Views
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 April 2017
    We stayed with friends on New Years Eve in this beautiful terraced cottage. The experience was amazing: Portland Bill seems to exist in a time warp and I will always remember...
    Reviewed 31 March 2017
    We have stayed here 3 or 4 times and always had a lovely time. The house is a very pretty old traditional Portland Stone building. It is in a no through road so very quiet...
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    About this property
    Built in the 1800's, this sweet little original Portland stone Fisherman's cottage promises a lovely holiday experience.Artist Cottage sleeps four people in two bedrooms and has been delightfully restored.The cottage is found in Fortuneswell just five minutes from the National Sailing Academy and a...
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    Location Information
    Isle of Portland, Dorset
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    The Gift House, a historic Seaman's Chaplaincy1 / 22
    (3)Very good
    0.3 kilometres from Portland Castle
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Cable/satellite TV
    • Private Garden
    • Central Heating
    • Ocean Views
    • Wi-Fi
    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 January 2018
    We stayed at the Gift House over Christmas / New Year and enjoyed staying, the accommodation was well equipped and generally well maintained.Our party consisted of two...
    Reviewed 28 September 2017
    We stayed at The Gift House for 4 nights last week and loved the house so much! It has everything you could need and is really nicely decorated with lots of quirky additions...
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    About this property
    The house is a late Georgian stone house located in the middle of island village, facing the sea. All 4 double bedrooms, the lounge and dining room are having panoramic sea view. The house is fully equipped self catering and has everything you need for an unforgettable holiday. The house has...
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    Location Information
    Isle of Portland, Dorset
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Schooner Cottage - New This year!1 / 36
    (9)Very good
    0.9 kilometres from Portland Castle
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Central Heating
    • Wi-Fi
    • Ocean Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 days ago
    Schooner cottage has been beautifully restored, giving it the character of its Georgian past with modern amenities.My husband and I stayed on Portland for 4 nights.. The views...
    Reviewed 4 weeks ago
    This was our first visit to Portland and we had a brilliant stay. Our base was Schooner Cottage, a very quaint, very old fisherman's cottage which has been renovated to the...
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    About this property
    Schooner Cottage is a carefully restored Georgian fisherman’s house, located in Fortunes Well, Portland, Dorset. The cottage will offer you a relaxing wintertime retreat with a Danish hygge feel, where you can be cosy in front of a log burning stove. You will hear the westerly storm rage outside,...
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    Location Information
    Isle of Portland, Dorset
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Number 81 / 22
    (37)Excellent
    4.0 kilometres from Portland Castle
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Cable/satellite TV
    • Balcony
    • Wi-Fi
    • DVD Player
    • Washer
    • Central Heating
    • Ocean Views
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    We spent a week here in August with our (almost) grown-up children. The location was perfect: it's the quieter end of Weymouth, away from the busier main beach and the harbour...
    Reviewed 14 June 2018
    Wow! What an absolutely lovely little house in the most beautiful setting. We stayed here for a short break away and loved every minute. The views from the house were stunning...
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    About this property
    A wonderful self contained and well equipped self catering house with all of the modern amenities to make your stay a memorable one and just a stones throw from the sea. Perfectly located for the beach, town and habour. It sleeps 5 with 1 main bedroom with a double bed and ensuite,a twin bedded...
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    Location Information
    Weymouth, Dorset
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    Cliff Walk Cottage1 / 22
    (3)Very good
    4.0 kilometres from Portland Castle
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Central Heating
    • DVD Player
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    • Washer
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    Really nice house has everything you need for your stay away nice quiet area good parking good base for exploring the Weymouth Portland area
    Reviewed 2 weeks ago
    We were attending Weymouth and Portland sailing club for a sailing event and found this cottage perfect as only 10 min drive away and the house had everything we needed for the...
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    About this property
    Cliffwalk Cottage is a modern two bedroom house, which can sleep up to 4 people. The Property has WiFi and full gas central heating throughout. At the rear of the house there is a enclosed garden with patio and BBQ area with garden furniture and a clothesline. The lounge / diner : smart TV, Blu...
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    Location Information
    Isle of Portland, Dorset
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Marina Place Weymouth1 / 15
    (11)Excellent
    4.9 kilometres from Portland Castle
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Waterfront
    • DVD Player
    • Secure Parking
    • Housekeeping Included
    • Washer
    • Wi-Fi
    • Balcony
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 days ago
    This excellently furnished and decorated apartment would suit a family of two adults and one to three children. Unfortunately, my party was comprised four adults. Whilst the...
    Reviewed 4 weeks ago
    the apartment is impeccably clean lots of amenities dishwasher washing machine super comfy beds lovely views over the old harbour and the bowling green easy parking bay host...
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    About this property
    Marina Place Weymouth Is a modern fully equipped apartment that we have just acquired & are now running it as a holiday let. We already run a popular holiday apartment named Seaside, in Weymouth and you can see our reviews already on TripAdvisor. The apartment Is on the 2nd floor over looking the...
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    Location Information
    Weymouth, Dorset
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    0.7 kilometres from Portland Castle
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
    • Wi-Fi
    • Central Heating
    • Washer
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    4 Sea View offers the best of modern comforts with period character in a cottage just a short walk from the splendors of Chesil Beach & Cove on the Isle of Portland Dorset. Offering a fabulous kitchen and comfortable accommodation. A character cottage designed to sleep six in three bedrooms in a...
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    Location Information
    Isle of Portland, Dorset
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.6 kilometres from Portland Castle
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Private Garden
    • Central Heating
    • Washer
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This lovely holiday home sits in the heart of Fortuneswell, Portland a short stroll from Chesil Cove. Sea views can be seen from the property where in the evening the rear windows provide lovely sunset viewing. The owners of the property have made this holiday property a home and it offers...
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    Location Information
    Isle of Portland, Dorset
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Chiswell Cottage1 / 12
    (9)Excellent
    0.6 kilometres from Portland Castle
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Private Garden
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 September 2016
    The house looked good inside and was nicely decorated and well equipped in terms of crockery, glasses etc. On arrival at the house the bin was overflowing and the door and...
    Reviewed 20 August 2016
    We spent a week at Chiswell cottage, was exactly as we expected. There were 6 adults, 2 children and a toddler and we had plenty of room. The kitchen was brilliant with both a...
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    About this property
    A spacious, comfortable cottage in this pretty road, a short walk down to Chesil Beach and Cove, and being in a convenient position for The National Sailing Academy and Portland Harbour. A four bedroom cottage over three floors with views over Chesil Beach. There is a private, fully enclosed rear...
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    Location Information
    Isle of Portland, Dorset
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Ocean Studio Apartment OSA11- Portland,Dorset1 / 8
    (2)Terrible
    4.2 kilometres from Portland Castle
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Internet Access
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Studio Apartment situated on 2nd Floor , Maritime House, Southwell Business Park, Portland .(ex mod building converted to living accommodation with kitchenette & en-suite bathroom) . Local amenities are within 5-10 mins driving distance. Approx 10 minutes walks from famous Portland Bill Lighthouse...
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    Location Information
    Isle of Portland, Dorset
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Mermaid Cottage1 / 8
    (1)Excellent
    3.1 kilometres from Portland Castle
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • DVD Player
    • Private Garden
    • Washer
    • Central Heating
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 August 2017
    Our family all had a brilliant holiday, cottage comfortable, with everything we needed. Even a play room for the kids, trampoline & swings in the garden.No do's and dont's...
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    About this property
    Whether you are looking for that relaxing break, or here to sail or just time with the family this charming cottage would suit your needs. Nestled off Wakeham, you will agree this cottage is a real find. A charming cottage nestled just behind Wakeham, backing on to open land. This spacious...
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    Location Information
    Isle of Portland, Dorset
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Sky View1 / 23
    (19)Excellent
    4.5 kilometres from Portland Castle
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Parking
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 October 2017
    We stayed at Sky View in September 2017 and had a fantastic time. The information pack that Martyn has put together about the accommodation and the surrounding area is excellent...
    Reviewed 3 June 2017
    Had the loveliest time staying here with my daughter and 3 young children. The flat has everything you need and more. Would highly recommend and hope to come back next year.
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    About this property
    Well equipped quirky town-centre flat in Weymouth, Dorset.Modern, bright and airy top floor flat. Hall, two double bedrooms, spacious lounge/diner with TV/DVD player, well equipped kitchen with full sized oven, dishwasher, fridge, combi microwave, toaster, coffee maker etc. Large modern bathroom...
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    Location Information
    Weymouth, Dorset
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Sea Cat Cottage1 / 15
    (2)Average
    1.0 kilometres from Portland Castle
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 September 2015
    The apartment was a little hard to find, but we liked the neighborhood from the first moment. The view is incredible! When we sat foot into the apartment we had the pleasure to...
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    About this property
    A charming Portland Stone Cottage in the heart of Fortuneswell. Tastefully decorated and furnished it offers cosy accommodation, for four people. Public parking close by and you are just a short stroll from Chesil Beach, if you turn in the other direction and head up the hill you will arrive at the...
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    Location Information
    Isle of Portland, Dorset
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Ocean Studio Apartments OSA11A-Southwell, Portland1 / 22
    (10)Very good
    4.3 kilometres from Portland Castle
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • Wi-Fi
    • DVD Player
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 July 2018
    We stayed for 5 days in room 11 and loved it! This room has a stunning view of the sea and across Southwell and the East of Portland. I love the quirkiness and history of...
    Reviewed 10 August 2017
    Had 13 lovely quiet days here. The room was very clean and tidy with all the facilities that were advertised.There is a good bus service stopping a few minutes walk outside to...
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    About this property
    Self contained apartment base on Southwell business park , isle of Portland. A short stroll from famous Portland bill& Jurassic coastline. Come &see for yourself Towels,Linens ,Toiletries provided equipped with hair dryer,iron+board ,fridge,toaster,kettle,Microwave oven. Tesco & co-op & local...
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    Location Information
    Isle of Portland, Dorset
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Ocean Studio Apartments OSA7- Portland Dorset1 / 15
    (1)Average
    4.3 kilometres from Portland Castle
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Parking
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 May 2016
    All was as we expected from the reviews. It is a building site but once inside it is very pleasant and has all we needed for our stay.Week end was lovely and quiet but mid week...
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    About this property
    If you are looking for the perfect place for a romantic weekend break for two, a longer get-away-from-it-all holiday or fun time with a group of friends then you've found it! Every apartment combines quality overnight comfort and en-suite facilities with modern self-catering kitchenette. The Ocean...
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    Location Information
    Isle of Portland, Dorset
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Chesil Holiday Lodge, Weymouth1 / 24
    (7)Excellent
    2.9 kilometres from Portland Castle
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Central Heating
    • Washer
    • Balcony
    • Sauna
    • Ocean Views
    • Wi-Fi
    • Parking
    • Shared Indoor Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    Stayed with our 9 and 12 year old, their response when we opened the door was wow. The static van was amazing and not really like a van at all. Lovely bathrooms, games in the...
    Reviewed 23 April 2017
    As soon as you open the door to the lodge you will experience the " Wow Factor ".The lodge is in a stunning and quiet position of the park facing the fleet lagoon. It...
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    About this property
    **sea views ** A luxury 2 bedroom (sleeps 6) holiday lodge situated on the 5 star Chesil Vista Holiday Park, near Portland and Weymouth Dorset. The lodge is located near the coastal path and has elevated sea views directly over Chesil Beach and Fleet Lagoon. Guests can make use of the park...
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    Location Information
    Weymouth, Dorset
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.9 kilometres from Portland Castle
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Wi-Fi
    • Ocean Views
    • Central Heating
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming three bedroom cottage ticked away a pebble's throw from Chesil Beach. Coral Cove is found between Sea View and Coastguard Cottages at the north end of the island. Ideal as a base for sailing, walking, diving and exploring the island and the rest of the county of Dorset. Vibrant night...
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    Location Information
    Isle of Portland, Dorset
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    3.3 kilometres from Portland Castle
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Parking
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A two-bedroom bungalow set in a unique coastal park within the grounds of a castle offering total relaxation and a fantastic coastal location. The site is ideal for a place to rest your head after a day on the water or if you are looking for a relaxing quiet break by the sea. This holiday home...
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    Location Information
    Isle of Portland, Dorset
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    0.8 kilometres from Portland Castle
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Central Heating
    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A sea side cottage situated a short stroll from Chesil beach and the Cove Inn, at the heart of Fortuneswell within a short distance of the Jurassic Coastline and National Sailing Academy at Portland Harbour. At the front of the property is an ideal place to relax with a cocktail under your own...
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    Location Information
    Isle of Portland, Dorset
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2.4 kilometres from Portland Castle
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Grill
    • Wi-Fi
    • Private Garden
    • Patio
    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Guillemot Cottage is a three storey terraced cottage in the heart of the small village of Easton and is a wonderful base for exploring Portland, Weymouth and the scenic Chesil Beach. The Cottage is newly refurbished over three floors. On entering the cottage you will find yourself in a cosy...
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    Location Information
    Isle of Portland, Dorset
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    5.0 kilometres from Portland Castle
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come and stay in our comfortable Willerby Rio caravan. The double glazing and central heating make it ideal for those out of season breaks. The caravan sleeps 6 in a high degree of luxury and comfort. The separate kitchen space has free standing table with a wrap around bench seat, gas oven/hob,...
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    Location Information
    Chickerell, Weymouth
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Two bedroom holiday bungalow1 / 8
    (12)Excellent
    3.4 kilometres from Portland Castle
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
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    Reviewed 2 weeks ago
    Perfect cottage in a great location on the isle of Portland. Our second stay on the island but our 1st stay in this cottage and we'll definitely come back to the cottage again...
    Reviewed 11 June 2018
    This is our 2nd visit to this bungalow and as before Lesley the owner is a lovely lady, she meet us there. The little touches makes it so welcome tea, coffee, milk and a lovely...
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    About this property
    A comfortable terraced bungalow with lounge/diner, kitchen and patio area in grounds near to Pennsylvania Castle so ideal for anyone attending functions there. Portland is a nature lovers paradise particularly of interest to birdwatching enthusiasts also to sailors as the National Sailing Academy...
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    Location Information
    Isle of Portland, Dorset
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    CARAVAN - WEYMOUTH1 / 4
    (6)Very good
    4.2 kilometres from Portland Castle
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Internet Access
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    The location is on a hill so can see the sea only a short drive to Weymouth and Portland which was perfect. Lovely facility well equipped kitchen has everything we needed and...
    Reviewed 2 June 2018
    The site is about 10 minutes drive from Weymouth. The site itself is on the side of a hill and is close to the South West Coast Path. There are views over Portland and Chesil...
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    About this property
    Our caravan is a bright and airy Wiilerby Eco Salsa. It is decorated and furnished to a good standard and can sleep up to 8 guests a double master bedroom plus 2 twin bedrooms sleeping 2 people in each. In addition there is a double bed settee in the lounge. Outside there are chairs and a table on...
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    Location Information
    Weymouth, Dorset
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Admiralty House1 / 22
    (28)Very good
    4.8 kilometres from Portland Castle
    7 Bedrooms, 5 Bathrooms, Sleeps 26 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • Central Heating
    • Parking
    • Private Garden
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 days ago
    Fantastic! Just come back from a lovely memorable family weekend age range 11 to 90 great location perfect for our needs including two dogs loved all sitting round the large...
    Reviewed 4 weeks ago
    As a big party for hen do I was struggling to find some where and then when I found this it was perfect. The house has everything you need for a weekend away. Good size kitchen...
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    About this property
    Weymouth has so much to offer. This seaside town has cinemas, a theatre, a Sea-Life centre, the restored fort, a swimming pool complex, a ten pin bowling alley. The list goes on. A trip to Weymouth wouldn't be complete without experiencing the Jurassic coastal walks. You may even discover a...
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    Location Information
    Weymouth, Dorset
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 26
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    Luxury 5 Bed Apartment + Sea View + Shower Room/WC + Kitchen + FREEPLAY Games1 / 27
    (2)Very good
    5.0 kilometres from Portland Castle
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • Wi-Fi
    • Central Heating
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    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 July 2018
    The location was the best thing about this place. It takes about 2 mins to walk to the sea, there's a nice gastro pub at the end of the road and it's close to all the shops. The...
    Reviewed 5 July 2018
    This room is in a great location and I feel if the description was a little more honest I would have given it a higher rating. I think that it should be clearer that it is just...
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    About this property
    Our property is a Grade II Listed Georgian detached house and our luxurious apartment with sea view (from the side) is located on the second floor, comprising a bedroom/lounge, ensuite shower room with wc and basin, and kitchen in the adjoining room. Prime location, 1 min walk from Weymouth's...
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    Location Information
    Weymouth, Dorset
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 5
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