Dorset Retreats for 4 People
Give yourself and your family some TLC and book a break in a holiday cottage for 4 in Dorset. Explore this beautiful county by day and return to your own private retreat. A Dorset getaway is good for the heart and soul, and offers a great opportunity for everyone to catch up and spend quality time together.Read more
Summer getaway with long days on the beach, or winter retreat with toasty open fires and sofas perfect snuggling. Modern conversion with bubbling hot tub, or quaint cottage nestled in the heart of beautiful countryside. Wherever and however you envisage your getaway with your friends and family, let Classic Cottages help you create your dream holiday. Dorset is a county begging to be explored, so browse our list of 43 available cottages for 4 and let your Dorset faucet flow.
Dorset Getaways for 4
From country to coast, Dorset offers as much opportunity for relaxation as exploration. Gather your loved ones and dive straight in.
At Classic Cottages we pride ourselves on marketing the highest quality self catering cottages in Dorset. All are regularly inspected and are totally equipped with everything you could need and more during your stay. We will guide you through every step of the way, from start to finish. The only thing you need to think about? Kicking back and enjoying your holiday.
43 luxury self catering cottages that sleep 4 people in Dorset
7 nights from £566
Gamekeeper's Cottage
45232 bedroom cottage with outside pool near Dorchester, Dorset.
Second in a row of pretty terraced cottages, this stylish property has been newly renovated to a very high standard. Gamekeeper's Cottage is one of four at Dominey's Yard, nestled ...
7 nights from £566
7 nights from £566
Poacher's Cottage
45222 bedroom cottage with outside pool near Dorchester, Dorset.
Tucked away in the picturesque village of Buckland Newton, Poacher's Cottage is one of four gorgeous properties making up Dominey's Yard. Situated perfectly for exploring the beaut...
7 nights from £566
7 nights from £577
Tolpuddle Cottage
37523 bedroom thatched, dog friendly cottage in Tolpuddle, Dorset.
This pretty thatched cottage is in the tranquil historic village of Tolpuddle, just 15 miles from the World Heritage Jurassic Coast. An ideal base for a family holiday or perfect f...
7 nights from £577
7 nights from £600
Dairyman’s Cottage
20942 bedroom, rural holiday cottage near Shaftesbury, Dorset.
Located in an Area of Outstanding Natural Beauty, Hatts Farm is a working farm set in 150 acres on the picturesque Dorset and Wiltshire border. Dairyman's Cottage is a traditio...
7 nights from £600
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 £627
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. From the moment you pull into the driveway you will love...
7 nights from £627
7 nights from £653
Barbridge Cottage
18052 bedroom, rural holiday cottage near Bridport, Dorset.
With beaches, fossil hunting, walks and lovely pubs all around, Barbridge Cottage is the ideal home-away-from-home to explore West Dorset and the Jurassic Coast. Up a short, unm...
7 nights from £653
7 nights from £653 *
St Peter's Cottage
51353 bedroom thatched, dog friendly cottage near Dorchester, Dorset.
Dating back to the early 17th Century, this picture perfect, Grade II Listed thatched cottage sits in the heart of a rural Dorset village. Recently renovated by the owners, St Pete...
7 nights from £653 *
7 nights from £677
Halcyon Cottage
46932 bedroom cottage near the beach and Lulworth Cove near Dorchester, Dorset.
Less than two miles from Lulworth Cove, part of the only World Heritage Site in England, Halcyon Cottage is a pretty, detached stone cottage in the heart of the village of West Lul...
7 nights from £677
7 nights from £725
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 £725
7 nights from £756
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 £756
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