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Cosy escapes

Winter Breaks

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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.

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Seacombe
Langton Matravers
4.9/5
Nestled in the sleepy village of Langton Matravers proudly stands Seacombe, an exquisite 4 bedroom family home. This stunning link detached home could easily be the set to a photoshoot for Country Living magazine. Furnished with high quality new furniture, sumptuous duck down quilts, crisp white linen and beds so comfortable you will struggle to leave them, Seacombe is the holiday home you've been searching for. ?
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3rd - 6th November  £764.01
4th - 7th November  £764.01
4th - 6th November  £764.01
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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.
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4th - 7th November  £448.75
2nd - 8th November  £589.75
2nd - 6th November  £491.59
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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.
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1st - 4th November  £580.00
2nd - 5th November  £580.00
6th - 8th November  £580.00
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Ridgeview Cottage
Corfe Castle
5/5
Located in the sought-after National Trust-owned village of Corfe Castle, Ridgeview Cottage is a modern, detached, family home found moments away from many of Dorset’s prolific attractions.
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1st - 4th November  £370.00
4th - 6th November  £370.00
1st - 7th November  £542.50
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The Aspens
Swanage
4.8/5
Delightful light-filled family holiday home, situated just a stone’s throw from beautiful Swanage Pier.
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3rd - 6th November  £380.76
1st - 5th November  £429.85
3rd - 5th November  £380.76
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Purbeck Cottage (Kings)
Swanage
4.7/5
3 bedroom family home with two parking spaces and large covered patio to enjoy outside dining whatever the weather.
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5th - 8th November  £364.75
4th - 8th November  £396.25
3rd - 8th November  £542.50
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Gable Cottage
Corfe Castle
4.8/5
3 bedrooms. Located on a large corner plot, this light and airy family holiday home in Corfe Castle, offers comfortable furnishings and modern fittings. Conveniently situated close to the common and village amenities including the bakery, general store, tea rooms and pubs.
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1st - 4th November  £511.07
1st - 5th November  £579.79
5th - 8th November  £511.07
+18 more stays
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Forest Edge Ph9 Web Forest Edge image Forest Edge image Forest Edge image Forest Edge image Forest Edge image Forest Edge image Forest Edge image Forest Edge image Forest Edge image Forest Edge image Forest Edge image Forest Edge image Forest Edge image Forest Edge image Forest Edge image Forest Edge image Forest Edge image Forest Edge image Forest Edge image Forest Edge image Forest Edge image Forest Edge image
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.
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4th - 7th November  £361.60
4th - 8th November  £407.80
3rd - 5th November  £361.60
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Juniper Cottage image Juniper Cottage image Juniper Cottage image Juniper Cottage image Juniper Cottage image Juniper Cottage image Juniper Cottage image Juniper Cottage image Juniper Cottage image Juniper Cottage image Juniper Cottage image Juniper Cottage image Juniper Cottage image Juniper Cottage image Juniper Cottage image Juniper Cottage image Juniper Cottage image Juniper Cottage image Juniper Cottage image Juniper Cottage image Juniper Cottage image Juniper Cottage image Juniper Cottage image Juniper Cottage image Juniper Cottage image Juniper Cottage image Juniper Cottage image Juniper Cottage image
Juniper Cottage
West Lulworth
4.8/5
Juniper Cottage is a recently refurbished Victorian terraced cottage tucked away off the main road in the scenic village of West Lulworth, close to both Lulworth Cove and one of the Jurassic Coast’s most iconic features, Durdle Door. This two-storey, dog-friendly cottage accommodates up to 4 adults or a family of 5. The ground floor is an open-plan living and dining space with small, private front and rear gardens, upstairs are two bedrooms and a bathroom.
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5th - 8th November  £442.08
1st - 8th November  £600.25
1st - 3rd November  £442.08
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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.
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5th - 8th November  £343.75
3rd - 8th November  £458.50
5th - 7th November  £343.75
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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.
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1st - 4th November  £434.42
2nd - 5th November  £434.42
4th - 8th November  £491.59
+18 more stays
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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.
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5th - 8th November  £511.75
2nd - 5th November  £511.75
3rd - 7th November  £518.05
+12 more stays
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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.

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