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Chester Holiday Homes

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    Travellers to Chester are booking July dates now. Secure your holiday rental today, and have the perfect trip.
    All 27 Rentals in Chester
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    Chester
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Chester
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Serenity1 / 16
    (4)Excellent
    Chester
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Chester
    5 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    About this property
    Beautiful 5 bedroom quiet retreat in the village. Lovely back yard with upper deck, BBQ outdoor dining. Walk out basement Large semi circular driveway can accommodate up to 4 cars. Addiction parking on road. In the heart of the village, just a quick stroll to parks, restaurants, shops, lido salt...
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    Chester, Southwest Nova Scotia B0J 1J0
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 13
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    Breath taking Ocean Harbour Front 3 Bedroom 2 Bath1 / 34
    (1)Excellent
    Chester
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
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    • Balcony
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    • Terrace
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 April 2017
    This home is a real find right on the water in the heart of Chester. You are within walking distance to restaurants, shops, the Tancook Island Ferry and the Yacht Club. We fell...
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    About this property
    Breath taking Harbour Front 3 Bedroom 2 Bath Condo. Located on historic Chester Front Harbour. Private steps to the crystal clean water perfect for swimming in the summer months .The perfect mix. Master bedroom custom on suite with rain shower, walk in closet Recently renovated and excellent mix...
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    Chester, Southwest Nova Scotia B0J 1J0
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Chester
    2 Bedrooms, 4 Bathrooms, Sleeps 4 Quick View
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    About this property
    This 200-year-old carriage house is Chester’s hidden gem. Completely renovated by a renowned East Coast architect, this property is the perfect place to relax and get away. It is located in the heart of the Chester village, within walking distance from restaurants, Nova Scotia`s oldest pub The...
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    Chester, Southwest Nova Scotia B0J1J0
    Holiday Rental House - 2 Bedrooms, 4 Bathrooms, Sleeps 4
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    Chester
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Private Garden
    • Patio
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    • DVD Player
    • Grill
    • Satellite TV
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cozy 1 bedroom cottage with a loft in the heart of Chester. Newly renovated. Full kitchen, living room and bathroom. Beautiful gardens surrounding the property. Cable and Wireless Internet Provided. Not far from Chester's beautiful waterfront. In walking distance there is the Yacht Club, Captain's...
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    Chester, Southwest Nova Scotia B0J 1J0
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Chester
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    RENTAL DESCRIPTION: PRIVATE 2 BEDROOM COTTAGE NEAR HISTORIC LUNENBURG, MAHONE BAY & STONEHURST. A magical private cottage built on the rocks of Schooner Cove where eagles, osprey and seabirds fly by at eye level. Panoramic views from every window and the deck offers wonderful sunrises and sunsets....
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    Chester, Southwest Nova Scotia
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Chester
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    RENTAL DESCRIPTION: DELIGHTFUL WATERFRONT 2BR/2BA HOME IN CHESTER'S BACK HARBOUR W/DOCK. Chester Waterfront with Private Dock, 4-Star. Extraordinary Location. This delightful waterfront home, nestled on a private lane, has a fabulous view of Chester's sheltered Back Harbour. Surrounded by peaceful...
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    Chester, Southwest Nova Scotia
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Chester
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
    About this property
    RENTAL DESCRIPTION: Take in as much beauty as the undeveloped Nova Scotia waterfront has to offer, from this charming, private 2-story home. Located at the end of a winding private drive, this cape-style shingled cottage is sequestered in a pristine and natural setting of 3.75 acres with 300-ft of...
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    Chester, Southwest Nova Scotia
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    #30 Captains Watch Oceanfront Retreat, McGraths Cove  NS1 / 16
    (2)Very good
    Chester
    6 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • Waterfront
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    This very nice home on a great place in a nice and friendly comunity needs cleaning up inside. Dishes, kitchenware, pots and pans was dirty and bevore using we have to clean up...
    Reviewed 14 October 2016
    I've stayed in many VRBO properties over the year. This is the BEST equipped property in which I've ever stayed. It was well-stocked with condiments from previous guests...
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    About this property
    RENTAL DESCRIPTION: The locals say that Nova Scotia is the place where heaven meets earth, and nowhere is that more true than on this Peggy's Cove area oceanfront retreat. To see this 5 Bedroom 3.5 bath newly restored home and its picture-perfect sheltered cove, is to fall in love. It is a great...
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    Chester, Southwest Nova Scotia
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 10
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    Chester
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Waterfront
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    Pet friendly
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    Smoking allowed
    About this property
    RENTAL DESCRIPTION: This delightful single level bungalow cottage is nestled on Nova Scotia's amazing South Shore area of Green Bay. Here, you are directly across from a pristine white sand beach and close to Risser's Beach Provincial Park. Wake up to the sounds of the ocean and surf while enjoying...
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    Location Information
    Chester, Southwest Nova Scotia
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    The following rentals are within 15 kilometres of Chester.
    Loon Lodge on Mahone Bay Harbor with Famous Waterfront View! Boats and Bikes!1 / 20
    (1)Very good
    Mahone Bay
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Central Heating
    • Grill
    • Wi-Fi
    • Satellite TV
    • Washer
    • Waterfront
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 August 2016
    The hosts tried in every way to anticipate the needs of guests. I would have given 5 stars but we, unfortunately, chose a week during an extended drought and the water comes...
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    About this property
    NOTE: Loon Lodge was completely booked for July and August, 2016 and well into the fall. Contact us early if you want prime vacation weeks in 2017. The 3 Historic Churches on Mahone Bay Harbor are one of Canada's most famous views, and WATERFRONT, LOON LODGE ON MAHONE BAY HARBOR has the best view...
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    Location Information
    Mahone Bay, Southwest Nova Scotia B0J 2E0
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Mahone Bay
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Grill
    • Balcony
    • Central Heating
    • Wi-Fi
    • Parking
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Conveniently located on Main Street, Mahone Bay, this cozy cottage offers the privacy of a country getaway within a short walk from downtown Mahone Bay.<BR><BR>One bedroom, one bath, includes a kitchenette, spacious living area and large private deck. Equipped with microwave, double-burner cooktop,...
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    Mahone Bay, Southwest Nova Scotia B0J 2E0
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Cherry Lane Cottage Mahone Bay NS1 / 14
    (3)Very good
    Mahone Bay
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Waterfront
    • Grill
    • Wi-Fi
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 September 2016
    Jim and I have traveled extensively over the years, but seldom have we enjoyed our accommodation as much as Cherry Lane Cottage. It is charming, comfortable, well equipped and a...
    Reviewed 3 September 2014
    Cherry Lane Cottage is centrally located, the ideal size, clean and well-equipped. We really enjoyed our week there. There is lots to do in the Mahone Bay area (including...
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    About this property
    Cozy 2 storey cottage on a narrow, quiet lane in the heart of pictureque, tranquil Mahone Bay, Nova Scotia. Within walking distance to downtown, the waterfront, restaurants, bistros, coffee shops, pub, shopping, waterfront festivals and events. Fully equipped kitchen, private deck with BBQ, bed...
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    Mahone Bay, Southwest Nova Scotia B0J 2E0
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Far Far Away Guesthouse1 / 13
    (4)Excellent
    Mahone Bay
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Wi-Fi
    • Washer
    • Air Conditioning
    • Parking
    • Satellite TV
    • Grill
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 October 2016
    This house was a very cozy and comfortable base for our travels around Mahone Bay. When we first arrived we found it it was farther from Mahone Bay than we had anticipated, but...
    Reviewed 14 August 2016
    The Far Far Away Guesthouse was exactly what my family of three needed. It was far enough away from the hustle & bustle of the city, and a close drive to attractions. My 5...
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    About this property
    Far Far Away is a Canada Select 4 Star guesthouse located directly between Chester and Mahone Bay; a ten minute drive in either direction and 25 minutes to the UNESCO World Heritage Town of Lunenburg. The guest house shares a driveway with an early 1900s home and has oodles of privacy in the...
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    Mahone Bay, Southwest Nova Scotia B3J 2Y3
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Heritage Cape on Main Street Mahone Bay1 / 15
    (2)Excellent
    Mahone Bay
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Terrace
    • Central Heating
    • Wi-Fi
    • Parking
    • Private Garden
    • Grill
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 June 2015
    We stayed for a couple of nights and wish we could have stayed longer. The house is beautifully decorated, quaint and cosy. The bathroom and bedrooms were impeccable, the...
    Reviewed 13 June 2015
    Extremely cozy place. Beautifully decorated. Well equipted with essential kitchen tools. Top quality bed & bath linens. Very comfortable beds in both rooms. Lovely deck area...
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    About this property
    Conveniently located on Main Street, Mahone Bay, this updated Cape-style home offers the privacy of a country getaway within a short walk from downtown Mahone Bay. Two bedroom, one bath, full kitchen, spacious living room, dining room and laundry facilities. The backyard contains a large lawn area...
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    Mahone Bay, Southwest Nova Scotia B0J 2E0
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    Mahone Bay
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Grill
    • Internet Access
    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    RENTAL DESCRIPTION: UPDATED OCEANFRONT 2BR/1 BA COTTAGE ON 35-ACRES W/POOL IN MAHONE BAY. Simply delightful, these three (3) refurbished oceanfront cottages on 35-acres with private swimming pool, will steal your heart. Beautifully upgraded, each cottages features one floor living with a bright...
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    Mahone Bay, Southwest Nova Scotia B0J 2E0
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Mahone Bay
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
    About this property
    RENTAL DESCRIPTION: Relax and surround yourself with the calming ocean views of Emily's Seaside Escape. Early riser's can savour their morning beverage on the spacious deck awakening to the glorious sunrise over St. Margaret's Bay. Watch as the sailboats and fishing vessels venture off to seize the...
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    Mahone Bay, Southwest Nova Scotia B0J 2E0
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Western Shore
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    • Private Garden
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed yesterday
    The owner Jay did an outstanding job of ensuring the unit was well stocked with everything. This included local organic coffee and local wine. There was really nothing that was...
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    About this property
    Over The Way Cottage offers pet-friendly accommodations in Martin's Point, Nova Scotia. It's conveniently located between Mahone Bay and Chester. Close to local attractions but out of the way enough to feel like a rural retreat. Originally built in the early 1900s, by the owners great grandparents,...
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    Western Shore, Southwest Nova Scotia B0J 2E0
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Mahone Bay
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Waterfront
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    RENTAL DESCRIPTION: DELIGHTFUL 2BR/1BA OCEANFRONT COTTAGE, UPGRADED W/POOL & PRIVATE DECK. Simply delightful, these three (3) refurbished oceanfront cottages on 35-acres with private swimming pool will steal your heart. Beautifully upgraded, each cottages features one floor living with a bright...
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    Mahone Bay, Southwest Nova Scotia B0J 2E0
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Mahone Bay
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Internet Access
    • Waterfront
    • Grill
    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    RENTAL DESCRIPTION: COZY SEASIDE RETREAT ON MAHONE BAY SLEEPS 6 W/PRIVATE DOCK & ROW BOAT. Silver Tides is a cozy and compact seaside retreat offering easy access to the sought after sailing waters of Mahone Bay. Special features include more than a 100- ft. of ocean frontage with rock-stone...
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    Mahone Bay, Southwest Nova Scotia B0J 2E0
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    #42 Kingfisher Cottage, Mahone Bay  NS1 / 14
    (1)Excellent
    Mahone Bay
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 September 2015
    This was our second time staying in this cottage. We stayed for 6 nights and wish we could have stayed longer. Very well equipped for cooking. Very quiet and peaceful...
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    About this property
    RENTAL DESCRIPTION: UPDATED OCEANFRONT 2BR/1BA COTTAGE ON 35-ACRES W/POOL IN MAHONE BAY. Simply delightful, these three (3) refurbished oceanfront cottages on 35-acres with private swimming pool will steal your heart. Beautifully upgraded, each cottages features one floor living with a bright open...
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    Location Information
    Mahone Bay, Southwest Nova Scotia B0J 2E0
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Mahone Bay
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    RENTAL DESCRIPTION: MAHONE BAY 2BR TOWNHOUSE IN TOWN NEAR ART GALLERIES, DINING, & SHOPS. The views from this second-level townhouse, located in the heart of Mahone Bay, are one of the most photographed scenes in Nova Scotia. From your waterside balcony, you look out onto the Mahone Bay Harbor and...
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    Mahone Bay, Southwest Nova Scotia B0J 2E0
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    The New-Found Guest House1 / 26
    (19)Excellent
    Mahone Bay
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Satellite TV
    • Grill
    • Shared Garden
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 July 2015
    My wife and I stayed at this cottage recently for two nights. We booked this property on the basis of the TA reviews although I didn't notice until after that, the most recent...
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    About this property
    The New-Found Guest House is located approximately 45 minutes from Halifax - Nova Scotia's capital, 5 minutes from scenic Mahone Bay and 10 minutes from historic Lunenburg - home of the Bluenose. This completely renovated loft suite is a fully-equipped, self-contained unit. It has two double beds,...
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    Location Information
    Mahone Bay, Southwest Nova Scotia B0J 2E0
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    #19 Saracenia Cottage, Upper Blandford  NS1 / 18
    (3)Very good
    Blandford
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    RENTAL DESCRIPTION: WATERFRONT 4BR/2BA CAPE HOME W/BOLD OCEAN VIEWS NEAR HISTORIC TOWNS. Saracenia Cottage is enjoying a second lease on life. This fabulous classic waterfront cape on a private paved road, has been loving restored with every modern amenity to make your stay here special. Located in...
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    Location Information
    Blandford, Southwest Nova Scotia
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Chester Basin
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    The spacious flat is private and has a great outdoor space too. It shares the grounds with Westaway House Bed and Breakfast although it's in a separate building. There are views to the water from every room. The flat has a large queen bedroom, modern spa-like bathroom and combined fully outfitted...
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    Location Information
    Chester Basin, Southwest Nova Scotia B0J1K0
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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