Enjoy Our Rural Cottage Retreats in Dorset
Put the breaks on the rush of every day life and take some time for yourself. A rural retreat in Dorset gives you the time for reflection and some much needed TLC. Pick the holiday of your dreams and soak in the sights and fresh, clean air. Once you've arrived at your perfect cottage, enjoy total comfort in your very own home from home. A country getaway in Dorset can't be beaten. Read more
For an escape to the country, Dorset is at the top of the list. Durdle Door, Lulworth Cove and the Old Harry Rocks are just the first things that come to mind, and there is plenty more to explore. With Dorset's naturally jaw-dropping aesthetics and with so much to see and do, you might be wondering what could make your holiday even better.
At Classic Cottages, we understand the importance of excellent accommodation to send your holiday from ordinary into the realms of fantastic. Every single one of our luxury rural retreats is personally inspected and fully equipped so that your self catering experience is the best possible. All that's left for you to do? Relax and enjoy.
Our exclusive ferry discounts will make your island trip with Classic plain sailing.
Select from 33 rural holiday cottages in Dorset
7 nights from £459
Old Sandpitts Cottage
45042 bedroom thatched cottage near Bridport, Dorset.
Tucked away down its own private track, this picture-perfect thatched cottage is a little gem. Surrounded by its own private garden, the cottage is very peaceful and offers space f...
7 nights from £459
7 nights from £491
The Old Coach House
13862 bedroom, dog friendly cottage near the county town of Dorchester, Dorset.
This pretty detached former coach house can be found in the rural Dorset countryside, within easy reach of the stunning coastlines of the Jurassic Coast, a World Heritage Site. ...
7 nights from £491
7 nights from £519
Celtic Blessing
22562 bedroom cottage near Bridport, Dorset.
Close to Dorset's spectacular Jurassic Coast, the popular market town of Bridport and the harbour and beach at West Bay, this cottage has stunning views of the gentle Dorset countr...
7 nights from £519
7 nights from £524
Ginny's Barn
52762 bedroom, character cottage close to the Jurassic Coast, near Bridport, Dorset.
Find your 'Far from the Madding Crowd' moment in the beautiful west Dorset countryside with a stay at Ginny's Barn. This characterful cottage offers compact, quaint accommodation, ...
7 nights from £524
Our property managers are local experts who handpick perfect places to stay.
Local experts
We scour the coast and country to winkle out bits worth sharing with you, the best properties in lovely locations. While we’re out and about, we gather together the best things to do so that you can start planning your holiday as soon as you’ve booked.
The ‘Explore Nearby’ tab on our cottage pages show what’s nearby along with relevant articles from our holiday guides from Notes and Stories, where you’ll find hand-written experiences of outings across the South and West, from dog-friendly pubs on the Isle of Wight to free things to do in south Devon and everything in between.
7 nights from £532
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 £532
7 nights from £548
The Old Dairy
47402 bedroom, dog friendly former milking parlour, near Blandford Forum, Dorset.
This former milking parlour that served the local farm has been beautifully converted into a fabulous holiday home. Situated in a picturesque Dorset village that is full of charact...
7 nights from £548
7 nights from £600
Dairyman’s Cottage
20942 bedroom, rural holiday cottage near Shaftesbury, Dorset.
Located in a National Landscape, Hatts Farm is a working farm set in 150 acres on the picturesque Dorset and Wiltshire border. Dairyman's Cottage is a traditional, semi-detache...
7 nights from £600
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 £694 *
Freshfields
57064 bedroom secluded cottage with large grounds 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 £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
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.
