Your search returned 231 cottages.
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- Sleeps8
- Bedrooms4
- PetsNo
Greenwell, a delightful house located in the town of Weymouth in Dorset boasting a Smart TV, woodburning stove and proximity to the beach and pub. (Ref. 1128598)
- Wi-fi
- Off-road parking
- Ground floor bedroom
- Dishwasher
- Washing machine
7 nights from £1015
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- Sleeps7
- Bedrooms4
- PetsNo
This pretty, detached cottage lies in Preston, Dorset. (Ref. 1119018)
- Wi-fi
- Off-road parking
- Dishwasher
- Washing machine
7 nights from £641
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- Sleeps8
- Bedrooms3
- PetsNo
On Weymouth Harbourside this is an extraordinarily spacious apartment, sleeps 8, tastefully renovated, Large en-suite showers to all rooms, harbour views, WiFi. (Ref. 994463)
- Wi-fi
- Dishwasher
- Washing machine
- Baby-friendly
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16% off - Thu 30th Oct 2025 to 3rd Jan 2026
7 nights from £979
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- Sleeps4
- Bedrooms2
- PetsNo
A contemporary, three-storey property resting by the harbour in Weymouth, Dorset. (Ref. 1058500)
- Wi-fi
- Dishwasher
- Washing machine
7 nights from £704
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- Sleeps6
- Bedrooms3
- PetsYes
Beautifully appointed cottage, resting in the quaint village of Sutton Poyntz in Dorset. (Ref. 1008404)
- Wi-fi
- Dishwasher
- Washing machine
- Baby-friendly
7 nights from £568
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- Sleeps4
- Bedrooms2
- PetsNo
A superb first-floor apartment resting in Weymouth, Dorest. (Ref. 1059262)
- Wi-fi
- Off-road parking
- Dishwasher
- Washing machine
- Baby-friendly
7 nights from £631
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- Sleeps4
- Bedrooms2
- PetsNo
This cottage boast style, character, and a fabulously contemporary interior. (Ref. 1005313)
- Wi-fi
- Dishwasher
- Washing machine
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£232 off - Mon 29th Dec 2025 to 5th Jan 2026
7 nights from £664
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- Sleeps4
- Bedrooms2
- PetsNo
This spacious ground-floor apartment is nestled in the gorgeous seaside town of Weymouth in Dorset. (Ref. 1037083)
- Wi-fi
- Off-road parking
- Ground floor bedroom
- Dishwasher
- Washing machine
7 nights from £502
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- Sleeps4
- Bedrooms2
- PetsNo
Sleeping 4 cosy cottage in Weymouth. (Ref. 994605)
- Wi-fi
- Off-road parking
- Dishwasher
- Washing machine
- Baby-friendly
7 nights from £594
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- Sleeps2
- Bedrooms1
- PetsNo
A delightful, one-bedroom holiday home resting in Weymouth, Dorset. (Ref. 1133982)
- Wi-fi
- Dishwasher
7 nights from £500
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Upwey is a beautiful little village nestled alongside the river Wey. Although it’s now part of Weymouth, Upwey has most definitely retained its village charm with everything you need for a wonderfully relaxing countryside retreat.
Walking through Upwey will take you past some beautifully unique houses and then through areas of completely open countryside. It is so tranquil and pretty that a break in a holiday cottage here will ensure that you leave completely relaxed.
It may be a small village, but Upwey is well known for its Wishing Well and Water Gardens. It is alleged that while unwell and staying in Weymouth, King George III would drink the water from the well, believing it to aid his recovery!
Upwey Wishing Well Tea Rooms is the perfect place for afternoon tea. They are big advocates of all things local so the ingredients they use are all of the finest quality from local Dorset producers. Stock up on the beautifully wrapped homemade jars of chutney and pickles to take back to your cottage to accompany your cheese and wine for the evening!
Upwey is home to some beautiful water gardens around the wishing well and it’s glorious here when the sun shines. Pick a spot for a picnic or just keep meandering along the garden pathways to see a new water garden, pond or waterfall at every turn. Don’t forget to make a wish at the wishing well before you leave!
Upwey even has its own 17th century traditional village pub, The Old Ship. It has a huge roaring fire to sit beside during the colder months and it lovingly welcomes well behaved dogs.
You really are in a fantastic location if you choose one of our Upwey holiday cottages. It feels like a world away from anywhere and almost has a ‘back in time’ feel about it, yet you are just 4 miles away from the award winning, golden sands of Weymouth beach, bustling Weymouth Harbour, superb restaurants and pubs and some great shopping. Weymouth is famous for putting on some fantastic events too! Weymouth Harbour plays host to the Wessex Folk Festival every year in June and Weymouth Carnival take place every August. If champagne and seafood takes your fancy, try the Dorset Seafood Festival, also in Weymouth Harbour in July.
A drive ten minutes inland from Upwey will take you to the wonderful market town of Dorchester. Head here for some great shopping, stunning architecture, Michelin starred restaurants and, if you are there for August bank holiday, try the annual French Market, where you can stock up on fine chocolates, baguettes, cheese and crepes.
You really can’t go wrong by choosing an Upwey holiday cottage for your break. We have some really beautiful Upwey self-catering holiday cottages to choose from. Be sure to check when booking if they are dog friendly, if you are bringing your four legged friend.