As frost delicately coats the Dorset countryside, the verdant leaves of meandering hedgerows are replaced with clusters of ruby-red berries, luscious holly, and winter-blooming flowers. The rugged coastline, usually bustling with summer visitors, is now a little quieter. And as you stroll along the coast path with your family or dog in tow, the rhythmic crashing of waves against the chalk-faced cliffs is a reminder of your welcomed winter escape after a long autumn stuck in the office. The sun doesn’t have to be at its warmest for our coastal county to be enjoyed. Browse our selection of winter holiday lets in Dorset for a festive short break to brighten those darker days.

Filter & Sort
{{ pagination.totalResults }}0 properties found
The Old Butcher’s Cottage
Corfe Castle
4.9/5
The Old Butcher’s Cottage is bursting with character. Recently renovated throughout, this high spec property is the hideaway you’ve been searching for. Luxurious furnishings and exquisite linens adorn the bedrooms, living area and kitchen, providing stunning accommodation that the whole family will remember. Parties of all kinds can enjoy home cooked meals in the large open plan kitchen-lounge area and gather around the dining table for drinks or a board game.
6
3
2
2
4th - 7th November  £511.75
3rd - 7th November  £518.05
3rd - 6th November  £511.75
+12 more stays
View & Book
Save 25% on stays between 24th May 2024 - 5th Jan 2025
3 Puddledock Cottage
Sutton Poyntz, Nr Weymouth
5/5
Enjoy soaking up the Dorset sunshine in this newly renovated countryside cottage, tucked away in the quiet village of Sutton Poyntz. 3 Puddledock Cottages is within a close proximity of Weymouth beach and local activities.
6
3
1
0
2nd - 6th November  £517.00 £435.00
2nd - 7th November  £620.00 £482.50
6th - 8th November  £456.50
+18 more stays
View & Book
Save 10% on stays between 1st Nov - 20th Dec
Little Westport
Wareham
4.8/5
Little Westport is a charming 1960s four-bedroom Colt House, in a peaceful setting with a large garden overlooking the Purbeck Hills. A perfect location for a break to enjoy walking, cycling or exploring the area.
8
4
2
0
4th - 7th November  £580.00
1st - 6th November  £715.75
3rd - 8th November  £715.75
+18 more stays
View & Book
Forest Edge
Sandford
4.8/5
Forest Edge is a two bedroom semi-detached chalet bungalow offering luxury accommodation near Wareham. Mainly laid out on the ground floor, this delightful holiday home has been completely refurbished to a very high standard.
4
2
2
2
3rd - 6th November  £361.60
3rd - 7th November  £407.80
4th - 6th November  £361.60
+12 more stays
View & Book
Bronte Cottage
Wareham
4.8/5
3 Bedrooms. Bronte Cottage is a charming holiday cottage in Wareham, hidden away in a fabulous location a few strides from Wareham Quay and the river Frome.
4
3
2
1
3rd - 6th November  £448.75
1st - 7th November  £589.75
3rd - 8th November  £589.75
+18 more stays
View & Book
Sea Reach
Swanage
4.9/5
2 Bedrooms. We are delighted to introduce Sea Reach, this spacious and modern ground floor apartment is in a prime holiday hotspot, just 3/4 minutes’ walk from the beach.
4
2
1
0
4th - 7th November  £434.42
2nd - 6th November  £491.59
2nd - 5th November  £434.42
+18 more stays
View & Book
Piona
Swanage
4.8/5
For a seaside break to remember, look no further! Piona is set in a prime location in the heart of Swanage in Dorset. You will have a wealth of attractions, amenities and the all-important sandy beach right at your fingertips – all just a 5 minute walk away!
6
3
2
0
2nd - 5th November  £419.09
4th - 7th November  £419.09
4th - 6th November  £419.09
+12 more stays
View & Book
Coastguard Cottage
Worth Matravers
4.6/5
A lovely semi-detached cottage in the much sought after village of Worth Matravers, within walking distance of the Jurassic Coast.
8
4
3
0
1st - 8th November  £568.75
View & Book
West Lodge
Nr Corfe Castle
5/5
Tastefully presented and finished to a high standard, this fabulous holiday home in Church Knowle, will appeal to those of you visiting with extended family and friends. Located just a mile outside Corfe Castle, as the crow flies between Kimmeridge Bay and the golden sands of Studland, you will be truly spoilt for things to see and do.
10
5
3
0
2nd - 5th November  £832.00
2nd - 6th November  £870.85
1st - 8th November  £1,041.25
+18 more stays
View & Book
Malvern Apartment
Swanage
4.5/5
This appealing large, ground floor apartment is part of a modern conversion of a former Edwardian hotel, right in the heart of the seaside town of Swanage in a quiet residential, tree lined street, less than 5 mins walk to restaurants, pubs, shops and the beach. You can enjoy a lovely glimpse view across Swanage bay from the lounge bay window.
2
1
1
0
2nd - 5th November  £343.75
4th - 8th November  £381.34
3rd - 7th November  £381.34
+12 more stays
View & Book
Save 15% on stays between 1st Nov - 20th Dec
Pembroke Cottage
Langton Matravers
4.7/5
Beautiful 19th century stone cottage offering a peaceful retreat to families and friends. Well situated in the village of Langton Matravers, this holiday home offers endless attractions and picturesque views of the countryside.
4
3
1
2
1st - 4th November  £448.75
1st - 3rd November  £448.75
1st - 7th November  £589.75
+18 more stays
View & Book
Castle View House
Corfe Castle
5/5
Escape the ordinary at Castle View House, a haven in the countryside that accommodates up to nine guests. With its enchanting views of Corfe Castle, stylish open-plan interiors, and dog-friendly atmosphere, this residence promises a unique and memorable retreat. Nestled in the heart of Corfe Castle village, it provides an ideal setting for switching off from the demands of everyday life and savoring every moment with friends and family. Whether you're captivated by the historic charm of the surroundings or indulging in the comfort of the stylish interiors, Castle View House invites you to create lasting memories in a tranquil and welcoming escape.
9
5
4
2
3rd - 6th November  £970.97
1st - 7th November  £1,324.75
1st - 5th November  £1,108.99
+18 more stays
View & Book
winter dog walk
Bring your companion

Pet-friendly winter holiday lets in Dorset

Your pets are an important part of your festive activities and for those seeking to share a winter short break in Dorset with their four-legged friend, our selection of pet-friendly holiday cottages ensures no family member is left behind. Picture wandering through the frost-dusted hills of Purbeck with your faithful dog bounding happily beside you. Alternatively, imagine enjoying a brisk walk along one of our deserted beaches; the salty breeze kisses your cheeks as your dog runs in and out of the lapping waves.  Many of our cosy cottages and coastal retreats warmly welcome pets, with amenities and spacious surroundings tailored to ensure a comfortable stay for both you and your dog.

christmas tree at holiday home ready for a festive short break
Getaway to the countryside

FESTIVE SEASON BREAKS

Nestled between rolling hills and weathered coastline, the county of Dorset beckons tourists with an abundance of seasonal offerings. As you walk through one of our quaint market towns, the scent of mulled wine wafts through the frost-kissed air and the cosy pub offers warm refuge from the winter chill, its crackling hearths inviting guests to unwind with a mug of steaming hot chocolate.

For those who wish to venture into the countryside, whimsical landscapes unfold like scenes from a storybook, revealing hidden valleys and ancient woodlands waiting to be explored. Clifftops adorned with seasonal greenery and their calm sandy beaches below also provide an enticing backdrop for leisurely strolls with the entire family. Whether you’re heading out of the city for a short coastal stay or looking for a holiday cottage to spend time with your loved ones during the festive season, we can help you find a perfect winter let in Dorset.

bike on a summer evening
Cosyup this winter

Romantic winter short breaks in Dorset

The crisp winter air carries the faint scent of wood smoke from distant cottages and the desire to curl up in front of a cosy wood burner is very, very tempting. As the daylight fades and the evenings become shorter, our idyllic Dorset holiday cottages are the perfect backdrop for couples to snuggle close and share quiet conversations over a glass of fine, artisan wine. Our selection of winter short breaks in Dorset offers postcard-perfect retreats and boutique hideaways for stolen kisses and shared memories this festive season. Walk hand-in-hand through streets studded with Christmas lights or enjoy a locally made, candle-lit dinner in a charming restaurant nearby. Dorset sets the stage for an unforgettable romantic escape during these colder months and our variety of smaller cottages and winter lets perfect for couples are the perfect place to stay.