Your search returned 480 cottages.
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- Sleeps4
- Bedrooms2
- PetsNo
A beautifully furnished annexe cottage on the edge of the little hamlet of Hazelbury Bryan in Dorset. (Ref. 969185)
- Wi-fi
- Off-road parking
- Ground floor bedroom
- Dishwasher
- Washing machine
3 nights from Fri 5th Dec
was £436£381Secure your holiday with a 30% deposit* Book now -
- Sleeps4
- Bedrooms2
- PetsNo
A detached barn conversion set within the village of Long Bredy. (Ref. 998739)
- Wi-fi
- Off-road parking
- Ground floor bedroom
- Dishwasher
- Washing machine
- Baby-friendly
3 nights from Fri 5th Dec £493
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- Sleeps2
- Bedrooms1
- PetsNo
Lovely apartment nestled in the thriving Dorest town of Swanage. (Ref. 979371)
- Wi-fi
- Off-road parking
- Dishwasher
- Washing machine
3 nights from Sat 20th Dec
was £452£358 -
- Sleeps7
- Bedrooms3
- PetsNo
This all-ground-floor cottage rests in the charming seaside resort of Swanage on the Jurassic Coast of Dorset. (Ref. 1012027)
- Wi-fi
- Off-road parking
- Ground floor bedroom
- Dishwasher
- Washing machine
3 nights from Sun 30th Nov £653
Secure your holiday with a 30% deposit* Book now -
- Sleeps8
- Bedrooms4
- PetsYes
A traditional detached cottage nestled in tranquil farmland in the village of Hummer near Trent. (Ref. 1070465)
- Wi-fi
- Off-road parking
- Hot Tub
- Dishwasher
- Washing machine
- Baby-friendly
3 nights from Fri 12th Dec
was £1201£1022 -
- Sleeps4
- Bedrooms2
- PetsNo
The Hayloft is a versatile, characterful, quirky, and Grade II-listed home, perfect for families or friends at Lower Lye, in the Blackdown Hills AONB. (Ref. 1120037)
- Wi-fi
- Electric car charging
- Ground floor bedroom
- Hot Tub
- Dishwasher
- Washing machine
- Baby-friendly
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10% off - Fri 12th Dec to 19th Dec 2025
3 nights from Mon 8th Dec £484
Secure your holiday with a 30% deposit* Book now -
- Sleeps6
- Bedrooms3
- PetsNo
A beautiful terraced fisherman’s cottage resting in the coastal town of Weymouth, Dorset. (Ref. 1133009)
- Wi-fi
- Dishwasher
- Washing machine
- Baby-friendly
3 nights from Thu 1st Jan £492
Secure your holiday with a 30% deposit* Book now -
- Sleeps4
- Bedrooms2
- PetsYes
This beautifully-presented cottage rests in the village of Litton Cheney in Dorset. (Ref. 1021813)
- Wi-fi
- Off-road parking
- Dishwasher
- Washing machine
- Baby-friendly
3 nights from Sun 30th Nov £674
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- Sleeps2
- Bedrooms1
- PetsNo
The Shippon is a spacious and inviting home, with characterful yet chic features, perfect for a couples retreat at Lower Lye, in the Blackdown Hills AONB. (Ref. 1087064)
- Wi-fi
- Electric car charging
- Ground floor bedroom
- Hot Tub
- Dishwasher
- Washing machine
- Baby-friendly
3 nights from Mon 8th Dec £462
Secure your holiday with a 30% deposit* Book now -
- Sleeps8
- Bedrooms4
- PetsYes
Old Post Office is a contemporary, four-bedroom home resting rurally in Glanvilles Wootton near Sherborne, Dorset. (Ref. 1129395)
- Wi-fi
- Off-road parking
- Hot Tub
- Dishwasher
- Washing machine
- Baby-friendly
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5% off - Tue 14th Oct 2025 to 31st Jan 2026
3 nights from Mon 1st Dec £1307
Secure your holiday with a 30% deposit* Book now
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!