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.
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.
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.
4 bedrooms. A great base and comfortable family home. This substantial detached holiday home offers ample accommodation for the extended family in a seaside location. Lizards Rest is the perfect choice for accommodation for large groups in Swanage.
Settle into a lovely family holiday at Beach Approach. A two bedroom ground floor apartment. A flat walk will take you to Swanage beach and High Street, which is lined with cute cafés, boutiques, and fine restaurants. Beach Approach is perfect for families with top sights in easy reach: Swanage Railway is just a two minute stroll away; take a trip down memory lane on the vintage steam engine to the historic village of Corfe Castle.
3 bedrooms. Heathlands is a modern cottage, the ideal base for family holidays in Studland. This light and airy holiday home is a short walk from Studlands long sandy beach.
2 bedrooms. Cheeseman’s Cottage embodies all the distinct qualities of a quintessential English country retreat in Dorset. This ‘chocolate box’ thatched cottage, located on a quiet country lane is surrounded by a beautiful garden (mainly laid to grass) and enjoying rolling country views. This cottage lies in the quiet village of Muckleford, which is within easy reach of the coast and a wealth of attractions.
3 bedrooms. This beautiful four star holiday home is the ideal choice for a self catering holiday in Swanage. This home boasts large picture windows and is an unusual upside down house that takes full advantage of the views, across the seaside town of Swanage to the sea and the Isle of White beyond. WIFI.
4 Bedroom, 3 bathrooms. Stunning countryside views with sea glimpses. Tilshead is a beautifully designed home nestled within the lovely village of Langton Matravers. This exceptional, bespoke house was created to offer a practical yet luxurious, contemporary residence complete with large relaxing garden. Graded four star gold by Visit England, this luxury Dorset holiday cottage is ideal for large parties or families.
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.
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.
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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