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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Wareham 
4.8/5
Swanage
4.7/5
Sandford, Wareham
5/5
Swanage
4.8/5
Swanage
4.9/5
Swanage
4.7/5
Swanage
4.8/5
Swanage
4.9/5
Wareham
4.8/5
Lulworth Cove
4.8/5
West Lulworth
4.9/5
Swanage
4.5/5
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 dog-friendly holiday cottages in Dorset 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.
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.
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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