Winter Short Breaks in Dorset
469 properties found
469 properties found
123 On The Sea - The Eaves
Weymouth, Dorset
123 On The Sea – The Eaves is a delightful apartment resting in Weymouth, Dorset, featuring beach views, off-road parking, and nearby attractions.
- Wifi
- Baby Friendly
- Dishwasher
- Off Road Parking
Sat 28th Nov for 3 nights
£376
Village View
Burton Bradstock, Dorset
A romantic retreat resting within the village of Burton Bradstock.
- Wifi
- Baby Friendly
- Dishwasher
- Ground Floor Bedroom
- Off Road Parking
- Washing Machine
Sun 29th Nov for 3 nights
£498
Little Brook
Nottington near Weymouth, Dorset
A charming, stone-built property resting within the village of Nottington, Dorset.
- Wifi
- EV Charging
- Ground Floor Bedroom
- Off Road Parking
- Washing Machine
Mon 30th Nov for 3 nights
£552
Tiddlers Cottage
Uploders near Bridport, Dorset
This attractive, one-bedroom cottage resides in Uploders near Bridport, Dorset.
- Wifi
- Off Road Parking
- Washing Machine
Mon 1st Mar for 3 nights
£402
123 On The Sea - Victoria’s Place
Weymouth, Dorset
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.
- Wifi
- Baby Friendly
- Dishwasher
- Off Road Parking
Fri 4th Dec for 3 nights
£376
The Compass
Swanage, Dorset
This first floor flat is located in the lively town of Swanage in Dorset and can sleep two people in one bedroom.
- Wifi
- Dishwasher
- Off Road Parking
- Washing Machine
Sun 13th Dec for 3 nights
£368
Sixpenny Cottage
Upwey, Dorset
A beautiful cottage, located in a pretty village near to Weymouth, with private parking and wifi.
- Wifi
- Baby Friendly
- Washing Machine
Sat 28th Nov for 3 nights
£486
Roundham Cottage
West Bay, Dorset
A pretty converted property within the popular coastal town of West Bay, Dorset.
- Wifi
- Ground Floor Bedroom
- Off Road Parking
Sat 28th Nov for 3 nights
£567
Frome View
Wool, Dorset
Frome View is a one-bedroom property in Wool, Dorset, and a well-proportioned retreat for couples, perfectly positioned for coast and countryside views.
- Wifi
- EV Charging
- Off Road Parking
- Washing Machine
Sun 29th Nov for 3 nights
£652
Embassy
Brewers Quay Harbour, Dorset
Embassy is a wonderful, third-floor apartment in Weymouth, Dorset.
- Wifi
- Dishwasher
- Washing Machine
Sat 12th Dec for 3 nights
£448
Fountain Cottage
Weymouth, Dorset
A delightful cottage with charm and character but a modern touch.
- Wifi
- Baby Friendly
- Dishwasher
- Ground Floor Bedroom
- Off Road Parking
- Washing Machine
Sun 29th Nov for 3 nights
£512
Cliff Barn
Burton Bradstock, Dorset
A charming countryside dwelling resting in Burton Bradstock, Dorset.
- Wifi
- Dishwasher
- Ground Floor Bedroom
- Off Road Parking
Tue 8th Dec for 3 nights
£515
5 The Beaches
Weymouth, Dorset
A modern second-floor apartment in the popular Dorset resort of Weymouth.
- Wifi
- Dishwasher
Mon 30th Nov for 3 nights
£480
Thimble Cottage
Winterborne Stickland near Blandford Forum, Dorset
Thimble Cottage near Blandford Forum, Dorset, sleeps two guests in one bedroom.
- Wifi
- Dishwasher
- EV Charging
- Off Road Parking
- Washing Machine
Sat 28th Nov for 3 nights
£432
Burton Bay
Burton Bradstock, Dorset
Perfect couple romantic retreat in Burton Bradstock, Close to Hive Beach, 5 minute drive to Bridport,Welcomes pets.
- Wifi
- Baby Friendly
- Dishwasher
- Ground Floor Bedroom
- Off Road Parking
- Washing Machine
Sun 29th Nov for 3 nights
£510
The Pebble
Melbury Osmond near Yetminster, Dorset
The Pebble is a delightful holiday cottage in Melbury Osmond near Yetminster, featuring an enclosed garden along with the convenience of private parking.
- Wifi
- Dishwasher
- Ground Floor Bedroom
- Washing Machine
Sun 29th Nov for 3 nights
£396
Tipsy Turtle
Portland, Dorset
Tipsy Turtle is an inviting, ground-floor apartment in Portland, Dorset, close to the beach, offering open-plan living and an enclosed courtyard.
- Wifi
- Ground Floor Bedroom
- Off Road Parking
Sat 28th Nov for 3 nights
£442
6 The Beaches
Weymouth, Dorset
An impressive second-floor studio apartment on Weymouth's seafront.
- Wifi
- Dishwasher
- Washing Machine
Sat 28th Nov for 3 nights
£416
123 On The Sea - The Cubby
Weymouth, Dorset
The Cubby is a delightful first-floor apartment in Weymouth, Dorset, boasting a central location close to shops, pubs, beaches and coastal attractions.
- Wifi
- Dishwasher
Sat 28th Nov for 3 nights
£366
Monarch
Brewers Quay Harbour, Dorset
Monarch is a fabulous, third-floor apartment in Weymouth, Dorset.
- Wifi
- Dishwasher
- Washing Machine
Fri 4th Dec for 3 nights
£470
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!