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Pet Friendly Holiday Rentals in Upwey

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    Travellers to Upwey are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    26 Matching Rentals in the Upwey AreaView all 53 rentals
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    The Swallows1 / 12
    (3)Excellent
    Upwey
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    The Brambles1 / 12
    (3)Very good
    Upwey
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Upwey Cottage - Weymouth1 / 21
    (19)Very good
    Upwey
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    CASTERBRIDGE, superb semi-detached cottage, en-suite, Smart TV, dog-friendly, in1 / 20
    (2)Excellent
    Upwey
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Private Garden
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 November 2016
    We have just spent a long weekend here with two teenagers. Smart tvs and hairdryers in every bedroom are brilliant for families. Two very good sized bathrooms. Very well...
    Reviewed 1 April 2016
    Just spent a brilliant week here in this new modern cottage. Great location for our visit to walking the coastal paths - in fact very pretty walks straight from the door. Very...
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    About this property
    This wonderful semi-detached cottage in a courtyard location is situated close to Weymouth and sleeps six people in three bedrooms.Casterbridge is a quality semi-detached cottage, one of five on-site in a courtyard setting, on the edge of Upwey near Weymouth. This superb holiday home is set mostly...
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    DT3 5QD, Upwey, Weymouth
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    BRAMSHURST, superb terraced cottage, en-suite, dog-friendly, watersports nearby,1 / 15
    (1)Excellent
    Upwey
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
    • Private Garden
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 June 2016
    We had a fantastic weeks stay in this new, modern and fully equipped holiday home. It had everything we needed for a short break and we felt very at home. The location is...
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    About this property
    This wonderful terraced cottage is situated in a courtyard location, one of a group of five on the edge of Upwey near Weymouth and sleeps four people in two bedrooms.Bramshurst is a superb terraced cottage, the middle one of three, in a courtyard development of five holiday cottages, on the...
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    DT3 5QD, Upwey, Weymouth
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Upwey
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Garden
    • Washer
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This wonderful semi-detached cottage is situated in the village of Upwey, near Weymouth and sleeps four people in two bedrooms.Shepherd Oak is a quality semi-detached cottage, in a courtyard setting and is one of five on-site, 3.5 miles from Weymouth. This superb holiday home is set mostly on the...
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    DT3 5QD, Upwey, Weymouth
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Pretty three bedroomed cottage in rural location on scenic Jurassic Coast1 / 32
    (2)Excellent
    Upwey
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Parking
    • Cable/satellite TV
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 August 2018
    We stayed with our two children 2 and 16 and my mum and dad. The cottage was clean and well equipped. The bedrooms were a good size. We enjoyed sitting out the front in the...
    Reviewed 29 July 2018
    A lovely little cottage with everything we needed and in a lovely location. Ideal for visiting Dorset
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    About this property
    Our Dorset Coast family and pet friendly cosy traditional three bedroomed cottage with country walks on the doorstep is set in the pretty village of Upwey on the outskirts of the popular seaside town of Weymouth and close to the charming historic county town of Dorchester. We welcome one well...
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    DT3 5QB, Upwey, Weymouth
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    SNOOKS COTTAGE, woodburning stove, off road parking, garden, in Upwey, Ref 916911 / 31
    (5)Excellent
    Upwey
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Private Garden
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 July 2018
    Snooks cottage is everything holiday accommodation should be. Beautifully decorated, spotlessly clean and delightfully quirky. You have absolutely everything you need with...
    Reviewed 5 June 2018
    This cottage is without doubt set in beautiful surroundings the Quality I could not recommend highly enough without doubt a stunning little cottage with fixtures and fittings...
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    About this property
    This is a wonderful Grade II listed, 17th century thatched cottage, nestling opposite the village church in the picturesque Dorset village of Upwey, just four miles from Weymouth, and can sleep four people in two bedrooms.Snooks Cottage is a wonderful Grade II listed, 17th century thatched cottage,...
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    DT3 5QE, Upwey, Weymouth
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    The following rentals are within 10 kilometres of Upwey.
    Blagdon Lower Barn1 / 11
    (2)Excellent
    Winterbourne Abbas, UK
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
    • DVD Player
    • Washer
    • Parking
    • Central Heating
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 May 2016
    Absolutely stunning barn in a picturesque location, we couldn't have wanted a more peaceful trip. Exactly as it looks in the pictures. We would love to return.
    Reviewed 20 November 2015
    We have been staying at Lower Barn now for over 4 years and try to rent it 4 to 5 times a year we love it so much. It is situated on its own surrounded by stunning countryside...
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    About this property
    The barn is located two miles from the Dorset villages of Martinstown and Portesham, four miles from Abbotsbury and six miles from the expanse of Chesil Beach. Blagdon Lower Barn is totally secluded and is accessed via a 400m long drive from the road. An ideal location for an outdoor break in the...
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    DT2 9HY, Winterbourne Abbas, Dorset
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Sian's seaside static1 / 14
    (4)Excellent
    Chickerell
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Parking
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Patio
    • Washer
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 August 2018
    Stayed for a week in Sian's caravan, my second stay, and would stay again! Very clean, hosts are very helpful and friendly, the site that the caravan is on has lots to do, we...
    Reviewed 23 September 2017
    Nice, clean, well kept caravan.Very welcoming and helpful owner.surprised to see a few bits in fridge to get you started.Site was good with all amenities available as extra.
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    About this property
    This carefully maintained 2014 Burgundy Swift caravan is located within a two minute walk of the Jurassic Coastline, in the highly rated Littlesea Holiday Park. A mere 15 minute cycle from the seaside town of Weymouth, the combination of privacy provided by its serene location, and its...
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    DT4, Chickerell, Weymouth
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Wagon House, Bookham Court1 / 19
    (8)Excellent
    Charminster, UK
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Grill
    • Shared Garden
    • Washer
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    Cosy cottage, dog friendly with helpful hosts. Fantastic views from cottage and well stocked village shop. Great place for star gazing and peace and quiet.
    Reviewed 4 weeks ago
    The cottage had excellent amenities with sensational views. It was within 5 minutes drive from the well stocked shop and local pub serving hearty food, The owner was very...
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    About this property
    The Wagon House holiday cottage is the old converted Wagon House with a galleried ceiling exposing oak beams. Suitable for families or couples, this cottage is all on one level and has a large sitting room with a woodburner in an inglenook fireplace. It has a separate kitchen and a double (King...
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    DT2 7RP, Charminster, Dorset
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Corner Cottage Osmington Dorset Thatched 4 bedroom cottage near beach pub & shop1 / 33
    (3)Excellent
    Osmington Mills, UK
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Balcony
    • Patio
    • Washer
    • Wi-Fi
    • DVD Player
    • Grill
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 October 2018
    This lovely cottage is well-situated in Osmington with good access to local attractions and coastal walks. The beach is about a mile away and many good walks within a few miles...
    Reviewed 4 October 2018
    This was the perfect spot for my family break. The cottage is in a great location for exploring the area. We absolutely loved the local pub. The cottage was superb - the beds...
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    About this property
    Corner Cottage in Osmington (not Osmington Mills, but this website doesn't seem to recognise Osmington which is just half a mile away) is a beautiful thatched property which we bought in May 2016. It has a lovely sunny garden which gets the summer sun for most of the day. It has one kingsize bed...
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    DT3 6ET, Osmington Mills, Dorset
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Warmwell Holiday Park, Birch Lodge, near Weymouth, Dorset1 / 25
    (23)Excellent
    Warmwell, UK
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Wi-Fi
    • Central Heating
    • Parking
    • Terrace
    • Balcony
    • Shared Indoor Pool
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 July 2018
    we were welcomed by a crisp and spoteless lodge and the location was amazing and so many child friendly activities to do.The lodge is maintained to great standards and is so...
    Reviewed 20 July 2018
    Lovely lodge! Very nicely decorated, clean, had everything we needed. Which is a joy as usually dog friendly accommodation can be 'not so good'. Where it was located on the site...
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    About this property
    Beautiful high specification lodge, set in 40 acres of stunning woodland, on the ever popular Warmwell Leisure Resort. Wild deer roam on the park, as well as plenty of rabbits, squirrels and pheasants. There are three well stocked fishing lakes, an indoor swimming pool and children's play areas....
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    DT28JE, Warmwell, Dorset
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Spacious Rural Dorset cottage sleeps 6-8 with hot tub1 / 54
    (9)Very good
    Broadmayne, UK
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Central Heating
    • Wi-Fi
    • Grill
    • Patio
    • Housekeeping Included
    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 October 2018
    Really lovely cottage, very well equipped. Owners very friendly and helpful. The garden would be perfect for families, very surprising how far it extends. Only downsides were...
    Reviewed 23 July 2018
    Good holiday had by all, nice quiet location just a shame about the stuffy neighbours but there is always one isn't there, lovely pub close by and a lovely cottage
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    About this property
    Our Dorset period cottage is in Thomas Hardy country, near the Jurassic Coast and Dorchester; ideal for holiday rental with 4 bedrooms sleeping 6 plus a sofa bed for an extra 2 guests at £20 per person per night. Well behaved pets are also welcome; we charge an extra clean fee of £10 per night per...
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    DT2 8PF, Broadmayne, Dorset
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Lavender Lodge1 / 9
    (3)Average
    Winterbourne Abbas, UK
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Cable/satellite TV
    • Parking
    • Wi-Fi
    • Washer
    • Private Garden
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 October 2017
    Three of us enjoyed staying here for a week with our dog. Plenty of local walking areas. Central location for visiting other parts of Dorset and further afield. Spacious...
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    About this property
    Modern 2 bedroom bungalow annex featuring large hall with storage facilities for walking boots, a living area comprising lounge, dining area and kitchenette, and a large family sized bathroom. The main bedroom has plenty of space for a cot which we can provide as required. The second bedroom is a...
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    DT29LS, Winterbourne Abbas, Dorset
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Osmington
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Wi-Fi
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A wonderful character cottage idyllically situated next to the millpond in the lovely old Dorset village of Sutton Poyntz, just over a mile from the sea. The Space: A charming cottage in a peaceful village within easy reach of Weymouth and the Jurassic Coast Millstream Cottage is a charming...
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    DT3 6LW, Osmington, Weymouth
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    Dorset period cottage sleeps 61 / 18
    (14)Excellent
    Osmington Mills, UK
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Private Garden
    • Washer
    • Housekeeping Included
    • Central Heating
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 April 2018
    We loved this cottage, which as well as being beautiful had excellent facilities, was very comfortable and was very well equipped. It was perfect for our group of 4 adults...
    Reviewed 30 January 2018
    Had the most wonderful time at this beautiful cottage. Excellently equipped with everything we could have possibly needed, comfy beds, great bath and shower facilities and a...
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    About this property
    Melcombe Cottage is a beautiful 18C stone cottage in the heart of the quintessential Dorset village of Osmington surrounded by thatched cottages. It combines the quaint features of a period property with the conveniences of modern living having been extensively renovated. It has 3 bedrooms, two...
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    DT3 6EJ, Osmington Mills, Dorset
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Osmington Mills, UK
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This cottage sits on the edge of Osmington in Dorset and is able to sleep two people in one bedroom.Appletree Cottage is a welcoming two-person property based in the Dorset village of Osmington. It plays host to one bedroom which offers a double bed, there is also a bathroom, the cottage can sleep...
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    DT2 8NE, Osmington Mills, Dorset
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Broadmayne, UK
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A charming bungalow based in the village of Broadmayne, just outside of Dorchester, it can sleep four people.10 Knighton Lane is a bungalow within the charming village of Broadmayne, located two miles from the county town of Dorchester. It has two bedrooms, one with a king-size bed and one with two...
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    DT2 8EZ, Broadmayne, Dorset
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    The Granary1 / 8
    (2)Average
    Winterbourne Abbas, UK
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Secure Parking
    • Grill
    • Washer
    • Central Heating
    • DVD Player
    • Private Garden
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 June 2015
    In general it was very comfortable and had nearly all basic essentials. An iron and scissors should be essential as is a mop and basic cleaning equipment so you can leave as you...
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    About this property
    Little Glebe Farm is positioned on the edge of the open countryside, in a secluded setting. Our location offers excellent access to footpaths from its front door. Maiden Castle, The Hardy Monument and even the coast are within a day's tramp. It provides a perfect base for daytrips: Dorchester,...
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    DT29LS, Winterbourne Abbas, Dorset
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Charminster, UK
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The property is located 2 miles from Dorchester. Located down a single track road with fields in front and 5 country properties nearby it is quiet but not isolated. There is a public golf course adjacent to the property. It is possible to walk to Dorchester but a car is almost essential. There is a...
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    DT27SG, Charminster, Dorset
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Osmington Mills, UK
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Private Garden
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This delightful detached house is in the village of Preston near to Weymouth in Dorset and can sleep six people in three bedrooms. Tanzey Hollow is a lovely detached house situated in the village of Preston near Weymouth and the coast. The property sleeps six with three bedrooms, two of which are...
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    DT3 6DL, Osmington Mills, Dorset
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Millstream Cottage located in Sutton Poyntz, Dorset1 / 19
    (4)Very good
    Osmington Mills, UK
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 May 2018
    Lovely cottage, great location.Good size bedrooms and lounge.The kitchen was small . A squeeze fitting 7 adults and high chair around the kitchen table..The kitchen was...
    Reviewed 5 June 2016
    Great spot and nice cottage. Although expensive, it was an amazing location in an 18th c cottage in a beautiful village. One gripe only was that there was one shower ( en suite...
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    About this property
    Millstream Cottage is a charming detached cottage in the pretty village of Sutton Poyntz. It is set in beautiful Dorset countryside just a few minutes' drive from both the bustling Georgian seaside resort town of Weymouth and the dramatic Jurassic World Heritage Coast. With countless beaches,...
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    DT3 6LW, Osmington Mills, Dorset
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    Jasmine Cottage1 / 17
    (17)Very good
    Osmington Mills, UK
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Washer
    • Cable/satellite TV
    • Central Heating
    • Private Garden
    • Parking
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    Such a lovely cottage in a very quiet village! There was four of us and we each had our own room - and with three bathrooms it was a delight! The spacious kitchen was the hub...
    Reviewed 21 August 2018
    Jasmine cottage is in a very quiet location but is only a five minute walk to the local pub and a few miles away from the local beaches.The cottage accommodated our family of...
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    About this property
    Jasmine Cottage, which is Listed Grade II, is believed to date back to the early 16th century and is one of the oldest properties in the village. The cottage, which has locally quarried stone elevations under a thatched roof and has under gone extensive renovations in 2010 is now sporting 4...
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    DT3 6EP, Osmington Mills, Dorset
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    OLD SCHOOL, Grade II listed, en-suite, WIFI, Ref 9309561 / 17
    (3)Very good
    Broadmayne, UK
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 May 2018
    The old school in West Knighton, Dorset is a wonderful old cottage, comfortable, with lots of character and central in the village. The village itself is lovely olde world and...
    Reviewed 25 May 2018
    Loved the location of this charming cottage in a small, very friendly village. On arrival we found that we couldn't fit two large cars on the off street parking but the charming...
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    About this property
    A converted school building set near the town of Dorchester in Dorset, it can sleep six people in three bedrooms.Old School is a grade II listed building located near the market town of Dorchester in Dorset. It has three bedrooms comprising of a king size, a twin with an en-suite and another twin,...
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    DT2 8PF, Broadmayne, Dorset
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Osmington Mills, UK
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This semi-detached house is in the town of Preston near to Weymouth and can sleep five people in three bedrooms.Oceana is a lovely semi-detached house situated in the town of Preston just one mile from Weymouth in Dorset. The house can sleep five people and has one king-size double bedroom, one...
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    DT3 6DG, Osmington Mills, Dorset
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
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