Christmas Cottages in Dorset
Remember that film, The Holiday? This is the place to find cottages for Christmas that look just like that. Thatched roofs heavy with snow (or at least a generous sparkly frost) down winding country lanes, a roaring log fire and cosy sense of well-being. Those things were all present in that movie starring Kate Winslet and Cameron Diaz but all-star cast aside, Dorset has plenty of picture-postcard places to stay where you can live out your festive dreams. Read more
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.We have 36 self catering cottages for Christmas in Dorset
7 nights from £644
The Lookout
57632 bedroom, dog friendly apartment with sea views, near Studland.
In an elevated position with views out to Swanage Bay, The Lookout is a modern, stylish, first floor apartment for up to four lucky guests and their four-legged friend to enjoy. Th...
7 nights from £644
7 nights from £555 *
Freshfields
57064 bedroom self catering cottage near Dorchester, Dorset.
Freshfields is a truly outstanding property in a picturesque Dorset village. Recently renovated throughout, the house provides space and privacy for all the family. Just a short dr...
7 nights from £555 *
7 nights from £495 *
Bluebells
56242 bedroom, dog friendly cottage in walking distance of Bridport, Dorset.
Tucked away in a quiet location, yet just a stone's throw from bustling Bridport and the Jurassic Coast, you will find Bluebells. Situated at the end of a pretty row of cottages, t...
7 nights from £495 *
7 nights from £837
The Old Dairy
55512 bedroom, dog friendly cottage near Wimborne Minster, Dorset.
Situated within the southern neolithic ring of Knowlton Church and Earthworks and perfectly positioned under a Dark Sky Reserve, is The Old Dairy; a stylish and modern conversion t...
7 nights from £837
7 nights from £476 *
Pippins
53602 bedroom, dog friendly character cottage near Beaminster, Somerset.
Pippins is a picture postcard country cottage nestled in the charming Somerset village of North Perrott - not far from the Dorset border. This cosy home can cater for all of the fa...
7 nights from £476 *
7 nights from £472 *
Woodville Cottage
51513 bedroom, dog friendly home near the beach in Lyme Regis.
Woodville Cottage is a pretty and charming property, an annexe to a Grade II Listed Georgian building. Hidden away from the hustle and bustle of the elegant seaside town of Lyme Re...
7 nights from £472 *
7 nights from £1112
Acorns
48283 bedroom cottage in Corfe Castle, Dorset.
Set on a private, secluded plot, Acorns is a wonderful family holiday home. Recently renovated to a very high standard, this detached house in the historic village of Corfe Castle ...
7 nights from £1112
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20% off
10 Oct 2025 - 13 Oct 2025
£880.60 £704.48
7 nights from £556 *
Bay Tree Cottage
48353 bedroom, dog friendly cottage near Bridport, Dorset.
Situated in a sleepy west Dorset village, just a short drive from the spectacular Jurassic Coast, you will find this pretty terraced cottage. Bay Tree Cottage offers all the deligh...
7 nights from £556 *
We’re here to help you find your perfect place to stay 7 days a week.
Open 7 days a week
Call our office on 01326 555555, email hello@classic.co.uk or click on the live chat button in the bottom right of the screen to talk directly to someone who can help with choosing your holiday. If you have any questions or need a hand with the booking process, we’re happy to help.
After booking your holiday with us, you’ll receive your holiday details two weeks before your holiday. This also includes our emergency out of hours phone number for when the office is closed, so we’re never more than a phone call away!
7 nights from £462 *
Rectory Cottage
47952 bedroom cottage near Bridport, Dorset
Hidden away in the grounds of a Grade II Listed former rectory, this picture-perfect cottage is a delightful Dorset escape. As you pull into the spacious parking-area you will get ...
7 nights from £462 *
7 nights from £630
Fox Cottage
47121 bedroom stylish cottage in Beaminster, Dorset.
Tucked away in an oh-so-pretty part of historic Beaminster, Fox Cottage is a gorgeous retreat for two. As soon as you arrive at this picture-perfect terraced cottage, you will want...
7 nights from £630
Christmas getaways in Dorset are everything you'd hope with the rolling landscapes and miles of Jurassic coastline. Find frosty fossils at Charmouth and eat Christmas fudge at the end of the pier in Lyme Regis, or head around the harbour to Bournemouth for a big town day out.
Stay inland in a rural delight lit with Christmas lights and check out the Christmas markets for last minute pressies - Sherborne has a particularly good one, or head to a historical highlight and admire somewhere like Corfe Castle in all its wintry glory.
All these places are best discovered with man's best friend at your side, so plan Christmas breaks with dogs in mind. There's many a winter walk to discover across the county when you book a holiday cottage for Christmas in Dorset.
