Your search returned 393 cottages.
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- 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
3 nights from Mon 23rd Feb £682
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- Sleeps6
- Bedrooms3
- PetsNo
Luxurious wooden lodge in the village of Wedmore in Somerset. (Ref. 982512)
- Wi-fi
- Off-road parking
- Electric car charging
- Ground floor bedroom
- Hot Tub
- Dishwasher
- Washing machine
- Baby-friendly
3 nights from Sat 21st Feb £686
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- Sleeps2
- Bedrooms1
- PetsNo
This attractive, one-bedroom cottage resides in Uploders near Bridport, Dorset. (Ref. 1117867)
- Wi-fi
- Off-road parking
- Washing machine
3 nights from Mon 23rd Feb £402
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- Sleeps4
- Bedrooms2
- PetsNo
A stylish property resting in the resort of Weymouth, Dorset. (Ref. 1100742)
- Wi-fi
- Off-road parking
- Dishwasher
- Washing machine
- Baby-friendly
3 nights from Sat 21st Feb
was £789£484 -
- Sleeps2
- Bedrooms1
- PetsNo
A charming reverse-level cottage in the village of Upwey, Dorset. (Ref. 1072756)
- Wi-fi
- Off-road parking
- Ground floor bedroom
- Dishwasher
3 nights from Sat 28th Feb £532
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- Sleeps4
- Bedrooms2
- PetsNo
A well-presented barn conversion resting on the outskirts of Okeford Fitzpaine, Dorset. (Ref. 1137516)
- Wi-fi
- Off-road parking
- Ground floor bedroom
- Dishwasher
- Washing machine
3 nights from Sat 21st Feb £584
Book nowLast booked yesterday -
- Sleeps8
- Bedrooms4
- PetsYes
Unwind in this stylish countryside retreat with a private, screened hot tub, cosy woodburner, pool table and spacious enclosed garden. (Ref. 1070465)
- Wi-fi
- Off-road parking
- Hot Tub
- Dishwasher
- Washing machine
- Baby-friendly
3 nights from Mon 23rd Feb £1050
Book nowLast booked yesterday -
- Sleeps6
- Bedrooms2
- PetsNo
This stunning, two-bedroom abode is perched in Lytchett Matravers, Dorset. (Ref. 1084628)
- Wi-fi
- Off-road parking
- Hot Tub
- Dishwasher
- Washing machine
- Baby-friendly
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5% off - Thu 8th Jan to 28th Feb 2026
3 nights from Thu 26th Feb £732
Book nowLast booked 7 hours ago -
- 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
3 nights from Sun 22nd Feb £1232
Book nowLast booked 2 days ago -
- 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 Sat 21st Feb £693
Book nowLast booked yesterday
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!