Christmas and New Year cottages for 2026 in Dorset
Get ahead of the crowd and treat yourself to a festive getaway in 2026. Enjoy a walk on the beach, along the cliffs, or up on the moors before tucking in to your Christmas roast, welcoming in the New Year, or just settling in for a night in front of a roaring fire. Choose from our selection of luxury holiday cottages in Dorset. Read more
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.See our 29 self catering cottages for Christmas and New Year in Dorset.
7 nights from £1313
Hood's
60452 bedroom, dog friendly self catering cottage near Bridport, Dorset.
This stunning barn and milking parlour conversion is set within the glorious Dorset countryside, offering panoramic views across the Marshwood Vale and beyond. Hoods provides luxur...
7 nights from £1313
7 nights from £631
Loaf
60461 bedroom, dog friendly self catering cottage near Bridport, Dorset.
Loaf is a gorgeous and sympathetic restoration of an ancient Dorset granary with panoramic views across the Marshwood Vale. Its interiors are straight out of a magazine with design...
7 nights from £631
Hood's and Loaf at Kingsland Farm
7 nights from £1944
7 nights from £694
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 £694
7 nights from £431 *
The Dairy
56822 bedroom, dog friendly holiday cottage near Beaminster, Dorset.
A cosy single-storey cottage, a secret wood and wildflower meadow, all available to you in a location only a short drive of the World Heritage Jurassic Coast, are we tempting you y...
7 nights from £431 *
7 nights from £431 *
The Granary
56832 bedroom, dog friendly holiday cottage near Beaminster, Dorset.
Tucked away in a rural corner of west Dorset you will find The Granary; a single-storey cottage with a shared two acre woodland and wildflower meadow to while away holiday days in....
7 nights from £431 *
Whetley Farm
7 nights from £861
7 nights from £594
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 £594
We’ve been raising the standards of self catering holidays since 1977.
Our family ethos
Tony and Clare Tregoning started the business back in 1977 and their dedication to quality and excellence is at the heart of everything we do. Tony is sadly no longer with us, but we still adhere to their original ethos of finding holiday homes we would like to stay in and have slowly grown the company to find the best picks of properties across the counties. Plus Clare still drops in to keep us on our toes.
As an independent, family-run company, we wouldn’t expect you to stay anywhere we wouldn’t want to stay ourselves. And we’re pretty picky. We want you to walk into your handpicked holiday home and say ‘wow’, sit back and relax.
7 nights from £833
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 £833
7 nights from £544 *
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 £544 *
Dorset is a delightful holiday destination full of winding country lanes and picturesque landscapes, even in mid-winter making it a lovely place to spend Christmas and New Year in a cottage.
Settle yourself in a self catering cottage on the Jurassic Coast this Christmas and find fossilized stocking fillers on a Christmas Eve stroll along the beach. Strike out along the coastline once more in this beautiful part of the world on Boxing Day and return to the warmth and comfort of your luxury cottage for Christmas.
New Years Eve with a view is something to remember so find yourself a New Years cottage near Corfe Castle, have a short break by Wareham Quay or watch firework displays over the water from a place with a sea view. New Years in Dorset will make your celebrations all the more celebratory.
