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
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.Select from 30 rural holiday cottages in Dorset
7 nights from £363
Spring View Cottage
57831 bedroom cottage with countryside views near Dorchester, Dorset.
A sweet bolthole for two, Spring View Cottage is nestled in the beautiful Dorset countryside. Easily accessible but far enough away to feel like you have really escaped, this compa...
7 nights from £363
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20% off
18 Jul 2025 - 25 Jul 2025
From £579.00 £463.20
7 nights from £373
Owl's Nest Cottage
29421 bedroom, dog friendly cottage near Sherborne, Dorset.
This cosy, compact, delightful bolthole for two is set in a wonderfully tranquil hamlet in north Dorset with village shops and a choice of two pubs within two miles. Built in lo...
7 nights from £373
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 £377
The Linhay
26611 bedroom cottage near the beach near Bridport, Dorset.
The Linhay is a tucked away single-storey retreat – and an ideal base for exploring the wonderful coastline. The cottage nestles alongside the barns, with a fully enclosed gravel c...
7 nights from £377
7 nights from £400
The Dairy
26631 bedroom cottage close to the Jurassic Coast, near Bridport, Dorset.
The Dairy is another extremely comfortable single-storey cottage in this small and friendly farm development. This property has French doors to its own enclosed outside space – the...
7 nights from £400
7 nights from £412 *
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 £412 *
7 nights from £412 *
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 £412 *
7 nights from £412
Swallows' Rest
46441 bedroom, dog friendly cottage near Beaminster, Dorset.
The sleepy west Dorset countryside awaits you at this cute bolthole for two (plus your four-legged friends). Tucked away at the end of the owners' garden, this converted barn is hi...
7 nights from £412
7 nights from £415 *
Sturthill Stable
28293 bedroom, dog friendly barn conversion set within a working farm near Bridport, Dorset.
This beautiful barn conversion at the heart of a working farm is just inland from Dorset's spectacular Jurassic Coast and its beaches. The rural setting will please all the family ...
7 nights from £415 *
Arrive at your handpicked holiday home safe in the knowledge it’s been fully inspected.
Quality inspections
We check our holiday homes to ensure that everything is up to our high standards for your holiday, from provision of our above standard minimum inventory to how fluffy the towels are, we make sure you’ll have a comfortable stay.
Hardworking teams of housekeepers will have the place spick and span, ready for your arrival, so when you get there you can just relax.
7 nights from £419
Badgers Cottage
30141 bedroom, dog friendly cottage near Bridport, Dorset.
This pretty semi-detached cottage for two is nestled within an Area of Outstanding Natural Beauty (now known as National Landscapes) on West Hembury Farm. Badgers Cottage is an ...
7 nights from £419
7 nights from £478 *
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 £478 *
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.
