Your search returned 468 cottages.
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- Sleeps8
- Bedrooms4
- PetsYes
Stanley House is an exceptional harbourside cottage located in the heart of Weymouth, Dorset. (Ref. 1138865)
- Wi-fi
- Off-road parking
- Dishwasher
- Washing machine
- Baby-friendly
- Sky TV
3 nights from Fri 24th Jan
was £1185£903 -
- Sleeps6
- Bedrooms3
- PetsYes
Princess Beach House is a terraced, pet-friendly holiday cottage located in the seaside town of Swanage in Dorset near the beach and local amenities. (Ref. 1163474)
- Wi-fi
- Dishwasher
- Washing machine
3 nights from Tue 21st Jan £612
Secure your holiday with a 30% deposit* Book now -
- Sleeps6
- Bedrooms3
- PetsNo
Groves House is a lavish, reverse-level abode located in Castletown near Fortuneswell in Dorset, with an open-plan layout and only a short walk from a pub. (Ref. 1166808)
- Wi-fi
- Off-road parking
- Ground floor bedroom
- Dishwasher
- Washing machine
3 nights from Sat 8th Feb £452
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- Sleeps2
- Bedrooms1
- PetsYes
The Cabin at Little Timbers is a quaint, pet-friendly cabin well-positioned to nearby attractions in Ringwood, Hampshire, boasting a woodburning stove. (Ref. 1164457)
- Wi-fi
- Off-road parking
3 nights from Tue 21st Jan £374
Secure your holiday with a 30% deposit* Book now -
- Sleeps4
- Bedrooms2
- PetsNo
The Elbow is a charming house with period features and a garden, within the picturesque Dorset National Landscape in the village of Frampton in Dorset. (Ref. 1151302)
- Wi-fi
- Off-road parking
- Dishwasher
- Washing machine
- Baby-friendly
3 nights from Tue 21st Jan £520
Secure 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 Tue 28th Jan £401
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- Sleeps2
- Bedrooms1
- PetsNo
The Halt is a delightful, romantic holiday annex situated in the lovely little village of Maiden Newton in Dorset with a studio-style living space. (Ref. 1165359)
- Wi-fi
- Off-road parking
- Dishwasher
- Washing machine
3 nights from Fri 24th Jan
was £392£305Secure your holiday with a 30% deposit* Book now -
- Sleeps4
- Bedrooms2
- PetsNo
Harbour Retreat is an eclectic first-floor apartment close to the harbour and beach, with roadside parking, in the heart of Weymouth in Dorset. (Ref. 1164179)
- Wi-fi
- Dishwasher
- Washing machine
- Baby-friendly
3 nights from Tue 21st Jan £424
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- Sleeps10
- Bedrooms5
- PetsYes
The Cheesehouse is an exceptional, pet-friendly five-bedroom home resting in Litton Cheney, Dorset featuring 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 Tue 21st Jan £1048
Secure your holiday with a 30% deposit* Book now -
- 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 Wed 22nd Jan £1259
Avoid the flock of tourists with a short winter break in Dorset this year. Explore the breathtaking 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, or one of these cottages for the New Year if you're looking for a different kind of winter break.
If a winter short stay in Dorset is what you're looking for this year, then book online with Dream Cottages today!