Your search returned 483 cottages.
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- Sleeps3
- Bedrooms2
- PetsYes
A charming thatched roof character cottage resting in the village of Osmington, Dorset. (Ref. 1064960)
- Wi-fi
- Off-road parking
- Washing machine
- Baby-friendly
3 nights from Sat 30th Nov £447
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- Sleeps4
- Bedrooms2
- PetsNo
Braiders Rest is a charming cottage located in the centre of Bridport, a market town in Dorset, with a lovely open-plan layout and short walk to a pub. (Ref. 1136101)
- Wi-fi
3 nights from Sat 30th Nov £477
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- Sleeps10
- Bedrooms5
- PetsYes
The Cheesehouse is an exceptional, pet-friendly five bedroom holiday home resting in Litton Cheney, Dorset with a games room with pool, darts and bar area. (Ref. 1161994)
- Wi-fi
- Off-road parking
- Ground floor bedroom
- Dishwasher
- Washing machine
- Games room
3 nights from Fri 29th Nov £1020
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- Sleeps4
- Bedrooms2
- PetsYes
18 Chamberlaine Road is a lovely and welcoming abode, near a beach, situated in the heart of Weymouth, Dorset, only a short walk to a local shop and pub. (Ref. 1161457)
- Wi-fi
- Washing machine
3 nights from Sat 30th Nov £386
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- Sleeps15
- Bedrooms6
- PetsYes
Anchor House is a stunning, pet-friendly townhouse with a private hot tub in the heart of Weymouth, Dorset, close to local amenities and the beach. (Ref. 1105510)
- Wi-fi
- Off-road parking
- Hot Tub
- Dishwasher
- Washing machine
- Baby-friendly
- Games room
3 nights from Sat 30th Nov £1259
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- Sleeps4
- Bedrooms2
- PetsYes
Old Ropemakers Cottage is a characterful cottage with woodburning stove situated near the beach in the town of Bridport, Dorset and a pet friendly policy. (Ref. 1155307)
- Wi-fi
- Washing machine
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5% off - Fri 3rd Jan to 10th Jan 2025
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5% off - Sun 5th Jan to 31st Mar 2025
3 nights from Sat 30th Nov £445
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- Sleeps4
- Bedrooms2
- PetsNo
Splash, a lovely, terrace cottage lies in the heart of Weymouth, a seaside town in Dorset. (Ref. 1154894)
- Wi-fi
- Off-road parking
- Dishwasher
3 nights from Sat 30th Nov £620
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- Sleeps6
- Bedrooms3
- PetsNo
Winkle Cottage is a wonderful holiday home, set over three floors, situated in the popular coastal town of Weymouth in Dorset by the historic harbour. (Ref. 1140944)
- Wi-fi
- Dishwasher
- Washing machine
- Baby-friendly
3 nights from Sat 30th Nov
was £642£498Secure your holiday with a 30% deposit* Book now -
- Sleeps4
- Bedrooms2
- PetsNo
Harbour Retreat is a delightful three-storey cottage by the harbourside in Brewers Quay Weymouth, Dorset. (Ref. 1139963)
- Wi-fi
- Dishwasher
- Washing machine
3 nights from Fri 29th Nov
was £676£510Secure your holiday with a 30% deposit* Book now -
- Sleeps5
- Bedrooms2
- PetsYes
30 Fleet Street is a lovely, pet-friendly two bedroom cottage located in the delightful town of Beaminster, Dorset and can sleep up to 5 guests. (Ref. 1161403)
- Wi-fi
- Dishwasher
- Washing machine
3 nights from Fri 29th Nov £391
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Avoid the flock of tourists with a winter short break in Dorset this year. Explore the breath-taking countryside and coast in the crisp air with your loved ones.
Why Book a Winter Short Break in Dorset?
Enjoy the great outdoors this winter with an adventure to Dorset. Admire the sea-breeze as you explore Old Harry Rocks, Lulworth Cove, Durdle Door and the Golden Cap. Or if for an inland walk, you can see the seasons change at Wareham Forest and Upton Country Park.
After your hike, you can reward yourself in a traditional pub for a hearty meal. Later on, look forward to returning to your Dorset cottage, where you can spend quality time together. The next day, treat your family to a trip to Abbotsbury Subtropical Gardens to see exotic plants.
Or if that's not for you, immerse yourself in the past at a historic attraction. Wander around the National Trust site of Kingston Lacey, which looks even more magical in winter! There is also Lulworth Castle, Castle combe and Highcliffe Castle.
Places to Visit on your Winter Short Break in Dorset
Our Cottages are dotted around the most scenic parts of Dorset, perfect for exploring in the cooler months. Pull on your woolly hat and wander around the idyllic village of Burton Bradstock for a winter walk. Here you will have easy access to the stunning Jurassic Coast and 18-mile Chesil Beach.
Travel along the coastline to reach West Bay, Eype, Abbotsbury and West Bexington. Wanting a family day filled with fun? Visit the vibrant seaside towns of Weymouth and Swanage for a host of attractions.
Types of Winter Short Stays in Dorset
Discover a range of beautiful holiday homes in Dorset during your winter staycation. Gather your family together with dog-friendly cottages and large holiday homes.
And you can stay cosy and warm as you snuggle up in a cottage with an open-fire. If you like open-fires then you may want to try country cottages to find a rustic base for your adventure.
If a winter short stay in Dorset is what you're looking for this year, then book online with Dream Cottages today!