Your search returned 510 cottages.
REFINE SEARCH-
- Sleeps8
- Bedrooms4
- Pet FriendlyNo
30 Southdown Avenue is a stylish coastal retreat in Weymouth, Dorset, boasting lovely sea views, a hot tub, off-road parking, and ground-floor living. (Ref. 1209219)
- Wi-fi
- Off-road parking
- Ground floor bedroom
- Hot Tub
- Dishwasher
- Washing machine
3 nights from Sat 28th Nov From €1357
Book nowLast booked yesterday -
- Sleeps2
- Bedrooms1
- Pet FriendlyNo
123 On The Sea – The Eaves is a charming apartment overlooking the beach in Weymouth, Dorset, boasting off-road parking and ample nearby attractions. (Ref. 1133964)
- Wi-fi
- Off-road parking
- Dishwasher
- Baby-friendly
3 nights from Sat 19th Dec From €517
-
- Sleeps10
- Bedrooms5
- Pet FriendlyYes
Harbins Farm is a farmhouse dating back 200 years, in Glanvilles Wootton Near Sherborne, Dorset, pet-friendly with woodburning stoves. (Ref. 1200098)
- Pets go free
- Wi-fi
- Off-road parking
- Ground floor bedroom
- Dishwasher
- Washing machine
3 nights from Sat 5th Dec From €1224
-
- Sleeps4
- Bedrooms2
- Pet FriendlyNo
Beck House, a welcoming mews house within a secure gated development in the heart of Weymouth, just a short walk from the harbour, beach and amenities. (Ref. 1201741)
- Wi-fi
- Dishwasher
- Washing machine
3 nights from Sat 28th Nov From €576
Book nowLast booked 2 days ago -
- Sleeps4
- Bedrooms2
- Pet FriendlyYes
Tane, a welcoming, pet-friendly home in the heart of a sought-after Dorset village, offering proximity to the village pub and scenic walks and footpaths. (Ref. 1201891)
- Pets go free
- Wi-fi
- Off-road parking
- Ground floor bedroom
- Dishwasher
- Washing machine
3 nights from Sun 29th Nov From €567
-
- Sleeps6
- Bedrooms3
- Pet FriendlyYes
Fairways House is a welcoming, semi-detached home resting in the riverside town of Weymouth, Dorset, with close by shops, pubs, a garden, and parking. (Ref. 1177908)
- Pets go free
- Wi-fi
- Off-road parking
- Dishwasher
- Washing machine
3 nights from Sun 6th Dec From €828
-
- Sleeps5
- Bedrooms3
- Pet FriendlyNo
Cove Cottage is a well-located cottage in Weymouth, Dorset, boasting close proximity to the beach and easy access to local shops and nearby amenities. (Ref. 1094256)
- Wi-fi
- Off-road parking
- Washing machine
3 nights from Sun 29th Nov From €788
-
- Sleeps4
- Bedrooms2
- Pet FriendlyNo
Swanny View is a welcoming caravan featuring open‑plan living, enclosed decking with furniture, EV charging on‑site and easy access to local amenities. (Ref. 1201196)
- Wi-fi
- Off-road parking
- Ground floor bedroom
3 nights from Sun 29th Nov From €476
Book nowLast booked 2 days ago -
- Sleeps2
- Bedrooms1
- Pet FriendlyNo
123 On The Sea – Victoria’s Place is a beautifully appointed seafront apartment in Weymouth, Dorset, featuring beach views, private parking, and a bright open-plan layout. (Ref. 1133962)
- Wi-fi
- Off-road parking
- Dishwasher
- Baby-friendly
3 nights from Sun 3rd Jan From €554
-
- Sleeps10
- Bedrooms4
- Pet FriendlyNo
A beautifully-presented, single-storey abode residing in Lytchett Matravers, Dorset. (Ref. 1084629)
- Wi-fi
- Off-road parking
- Ground floor bedroom
- Hot Tub
- Dishwasher
- Washing machine
- Baby-friendly
3 nights from Sat 28th Nov From €1530
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!