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Pet Friendly Holiday Rentals in Chesterfield

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    Travellers to Chesterfield are booking January dates now. Secure your holiday rental today, and have the perfect trip.
    24 Matching Rentals in ChesterfieldView all 51 rentals
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    THE ROBINS1 / 26
    (12)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Runner Duck Cottage1 / 14
    (7)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Cavendish Cottage Ashover Derbyshire1 / 20
    (31)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Dog Friendly Spacious 2 Bedroom Apartment1 / 16
    (4)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Grill
    • DVD Player
    • Wi-Fi
    • Parking
    • Central Heating
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 August 2017
    Lovely, spacious first floor apartment. Kitchen fully stocked with all the utensils you could wish for and comfy beds.Had a great week.
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    About this property
    Pinewood Apartment is a very comfortable and spacious self-contained first floor self-catering holiday apartment. This property sleeps up to 4. The apartment has 1 double bedroom and 1 twin bedroom. It has a fully fitted kitchen, a large lounge and a bathroom with bath and overhead shower....
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    Ashover, Chesterfield S45 0BL
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Wood view lodge1 / 13
    (4)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Central Heating
    • Cable/satellite TV
    • Private Garden
    • Patio
    • DVD Player
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 August 2018
    Stayed here Mon-Fri. Fantastic base for exploring the Peaks. Very comfortable cottage with everything we needed. 2 lovely pubs within a mile or so (both called The Peacock...
    Reviewed 12 January 2018
    We love this place. The owners are fantastic, nothing is to much trouble. It's a real home will be going back again soon thank you so much for everything Karen and hubby. Jan x
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    About this property
    Two bedroom ground floor apartment..wheel chair access..open views to front..garden view to both bedrooms..large open plan kitchen/lounge/diner.. All furniture and decoration to high standard..very comfortable and light through out. Lovely decked area with seating and large table for out door...
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    Cutthorpe, Chesterfield S18
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Private Garden
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The property is a welcoming mid-terraced cottage located at the heart of Barlow,on the eastern edge of the Peak District National Park. The market town of Chesterfield is a short drive to many nearby attractions.  Within easy reach is the spa town of Buxton and the market town of Bakewell,famous...
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    Barlow, Chesterfield S18 7SL
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 4
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    Thorntree Lodge Thorntree Farm1 / 14
    (23)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 November 2018
    Just returned from a week at thorntree lodge, I travelled with my wife, 10 year old daughter and our Cockapoo dog, the lodge has everything you could need and is in a lovely...
    Reviewed 13 September 2018
    Wonderful accommodation and ideal base for lots of attractions. Chats worth, Matlock and Bakewell all close by and lots of English Heratige castles in the area too.
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    About this property
    New for 2017 Thorntree Lodge is a luxury three bedroom log cabin situated on a farm in a small hamlet, Uppertown in the parish of Ashover Derbyshire just a stones throw from the Peak District, The Lodge has a cosy open plan living area making it lovely and light with double doors opening onto a...
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    Ashover, Chesterfield S45 0JF
    Cabin Holiday Rental - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    SPRINGWELL FARM HOLIDAY COTTAGE, farmhouse, romantic, pet friendly, near Holymoo1 / 8
    (2)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 March 2018
    Had an amazing stay. The cottage is decorated to a very high standard and bed was incredibly comfy. Even with temperatures being very low nearly freezing the cottage was warm...
    Reviewed 7 September 2017
    Pretty central of activities in the area, and not far from supermarkets.Quality of equipment, furnishings, decorations, very good, central heating, so warm and comfy.A quite...
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    About this property
    This lovely ground floor studio is near to the village of Holymoorside near to Chesterfield in the Peak District and can sleep two in one bedroom. Springwell Farm Holiday Cottage is a lovely farmhouse conversion near to Holymoorside in the Peak District with uninterrupted elevated views of the...
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    Holymoorside, Chesterfield S42 7HW
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    THE BYRE, 200 year old cottage, parking, patio with furniture, in Ashover, Ref 91 / 6
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 August 2018
    I stayed here for the last 2 nights with my husband and our dog. The cottage is next door to the owners home and also has an adjoining cottage. It is very cosy and in a good...
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    About this property
    This cottage is a cosy retreat on the edge of the lovely village of Ashover in the Peak District and can sleep two people in one bedroom.The Byre is a cosy retreat on the edge of the lovely village of Ashover in the Peak District and can sleep two people. There is a super king-size double bedroom...
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    Clay Cross, Chesterfield S42 6AN
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    THE TACK ROOM COTTAGE, country location with charming views, character features,1 / 11
    (3)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 April 2018
    A beautifully decorated and well appointed spacious cottage, the perfect home from home. All 5 occupants during our stay were sad to return home! The photographs do not convey...
    Reviewed 31 December 2017
    Wow what a find! Beautiful converted barn, very high spec, beautiful decor. Everything has been thought of. Great location! Would love to live here! Peaceful surroundings and...
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    About this property
    This charming, three-bedroomed cottage in the village of Ashover, adjoins another holiday home on the owner's land and sleeps six people in three bedrooms. The Tack Room Cottage offers groups a great base for a holiday in this lovely area. Attached to a similar holiday home on the same site as the...
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    Location Information
    Ashover, Chesterfield S45 0DR
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Foxglove Cottage  -  Ashover near Matlock1 / 19
    (43)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Private Garden
    • Patio
    • Central Heating
    • Grill
    • DVD Player
    • Washer
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 January 2018
    We thoroughly enjoyed our extended Christmas break. We received a very warm welcome from Sue and Chris. The cottage was warm and cosy and the kitchen was particularly smart...
    Reviewed 24 August 2017
    Foxglove cottage is cosy, comfortable and has everything you might need. The area is so peaceful and there are lovely walks right from the front door. We enjoyed relaxing in the...
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    About this property
    Foxglove Cottage is full of character and is furnished and equipped to a high standard whilst retaining many original features. Foxglove sleeps four but we've discovered that it is a particular favourite with couples. This cosy stone cottage is on a quiet, private lane in a small farming village...
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    Ashover, Chesterfield S426AT
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Unwind in the peace and tranquillity in the heart of the charming Peak District village of Barlow. Barlow lies right on the eastern fringe of the Peak District National Park. Within easy reach is the spa town of Buxton and the market town of Bakewell,famous for the original Bakewell pudding. Spend...
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    Barlow, Chesterfield S18 7SL
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoying an idyllic position in the peaceful rural village of Barlow,Mulberry Cottage is a lovely property for those seeking a taste of village life amidst the outstanding natural beauty of the Peak District. Surrounded by excellent walking trails Mulberry Cottage offers guests a great base from...
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    Barlow, Chesterfield S18 7TE
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Unwind in peace and tranquility in the heart of the charming Peak District village of Barlow which lies right on the eastern fringe of the Peak District National Park. Within easy reach is the spa town of Buxton and the market town of Bakewell,famous for the original Bakewell Pudding. Spend days...
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    Barlow, Chesterfield S18 7SY
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    ACORN COTTAGE, pet friendly, character holiday cottage, with a garden in Ashover1 / 11
    (34)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
    • Private Garden
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 September 2018
    Great location down country road, like the little touches of the eggs and biscuits, very quiet stay, great rest for us, nice walks and maps provided, but be prepared to stay out...
    Reviewed 20 August 2018
    Arrived to find the cottage immaculately cleaned and with some lovely little welcoming touches from Veronica the owner. Fresh eggs and biscuits waiting for us on the table and...
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    About this property
    This stone-built Peak District cottage is located on the owners' working smallholding in the tiny hamlet of Brockhurst, 1 mile from the pretty village of Ashover in Derbyshire, and can sleep 4 people in 2 bedrooms.Acorn Cottage is a stone-built Peak District cottage, located on the owners' working...
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    Ashover, Chesterfield S45 0HR
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located only a mile from Chesterfield,guests are never far away from a wide selection of eateries and shops. A day spent bargain hunting at Chesterfield Market is a must,and the famous crooked church spire is well worth a visit. A short drive west will bring you to the sprawling Peak District...
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    Chesterfield, Derbyshire S44 5XH
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    THE OLD BLACKSMITHS, beautiful stone cottage, en-suites, parking, side patio, in1 / 7
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 September 2017
    Wow what a lovely cottage to stay so welcoming little home from home. Andrew the owner has thought of everything very clean, comfy beds well equipped kitchen. The cottage is...
    Reviewed 7 September 2017
    Three of us stayed for a week to, mainly, attend a wedding in Budby.This proved to be the perfect place for us all. Both bedrooms upstairs and both with own ensuite so we all...
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    About this property
    This cottage is a beautiful stone cottage on the edge of the lovely village of Ashover in the Peak District and can sleep four people in two bedrooms.The Old Blacksmiths is a beautiful stone cottage on the edge of the lovely village of Ashover in the Peak District and can sleep four people. There...
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    Clay Cross, Chesterfield S42 6AN
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    An end of terrace barn conversion just one mile from Barlow, near Chesterfield, and can sleep four people in two bedrooms.Rumblings 1 is an end of terrace barn conversion, just one mile from Barlow, near Chesterfield, and can sleep four people. There is a king-size double bedroom, a twin bedroom, a...
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    Barlow, Chesterfield S18 7SE
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This barn conversion is nestled close to the village of Ashover, near Matlock and can sleep four people in two bedrooms.Riber View Barn is a beautiful converted barn situated near the rural village of Ashover in Derbyshire. It boasts two bedrooms; a four poster bed and a double, sleeping four...
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    Ashover, Chesterfield S45 0JS
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    GARDENER'S COTTAGE, good touring base, flexible zip/link bed, multi-fuel stove,1 / 19
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    • Hot Tub
    • Parking
    • Wi-Fi
    • Private Garden
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    This cottage is PERFECT. Absolutely stunning little place, on a an even better piece of beautiful land! Ideal for the Peak District as close to many places to go.Fully...
    Reviewed 10 November 2017
    We stayed in this lovely little cottage for a week with our 2 kids and dog. The rooms are very spacious, the log fire lovely to come back to after a chilly day walking. The...
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    About this property
    A lovely holiday cottage in Clay Cross near Chesterfield, with two bedrooms accommodating three people. Gardener's Cottage is a lovely holiday home, set within two acres of grounds with Alma House, a Victorian gentleman's residence dating back to the 1875. The cottage has two bedrooms, a room with...
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    Clay Cross, Chesterfield S45 9PH
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 3
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Secure Parking
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Annexe is a stunning one bedroomed apartment set in picturesque grounds of Kneese Croft House. Tucked away in the country settings of Holymoorside, Chesterfield The Annexe is perfect for a peaceful getaway. There are also road links to Matlock and the Peak District for people looking for a...
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    Holymoorside, Chesterfield S42
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A detached chapel conversion situated on the outskirts of Ashover in Derbyshire, it can sleep two people in one bedroom.The Chapel is a nineteenth century conversion located just outside of Ashover in Derbyshire. It has a mezzanine king-size bedroom and a shower room, the property can sleep two...
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    Ashover, Chesterfield S45 0BL
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    This semi-detached cottage sits in the village of Clowne in Derbyshire, it can sleep four guests in two bedrooms.31 Rectory Road is a semi-detached house situated in the village of Clowne in Derbyshire. It benefits from two bedrooms which include a king-size zip/link and a twin, there is also a...
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    Clowne, Chesterfield S43 4BH
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Hagg Hill Hall1 / 38
    (175)Excellent
    8 Bedrooms, 7 Bathrooms, Sleeps 22 Quick View
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    • DVD Player
    • Hot Tub
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    • Central Heating
    • Patio
    • Private Indoor Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    Twenty two family and friends came together to celebrate my son's 21st and wife's 50th at this amazing old Manor House and its furnishings. With ages ranging from 2 to 72 this...
    Reviewed 2 November 2018
    Fabulous long weekend to celebrate my wife's 70th Birthday, accommodating eight family adults and eight grandchildren (ranging from 2 years up to 12 years).All facilities were...
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    About this property
    Hagg Hill House is filled with a wealth of antiques and luxurious furniture spread throughout the property, Hagg Hill Hall has 2 living areas with large sofas & flat screen TV's, A large dining room and garden room that both easily seat 22 . The kitchen has a large table that easily seats 10,...
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    New Tupton, Chesterfield S426JU
    Holiday Rental House - 8 Bedrooms, 7 Bathrooms, Sleeps 22
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