Cottages for the Summer Holidays in Dorset
Our self-catering holiday cottages come in all shapes and sizes for the school summer holidays. Hunt for fossils along the stunning Jurassic Coast, tuck into a delicious afternoon tea in a cool cafe sourced with local goods, stroll along the coast path or head inland and take up one of the many cycling routes, the choices are boundless.
We currently have 40 cottages available for you to choose from. Find your favourite now. Read more
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.Browse from 40 summer holiday cottages in Dorset
7 nights from £1021
Minnie's Cottage
61262 bedroom, dog friendly cottage near the beach near Bridport.
Minnie's Cottage is a cosy quintessential thatched cottage in the beautiful coastal village of Burton Bradstock. Situated in the heart of the village and just half a mile from the ...
7 nights from £1021
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20% off
3 Jul 2026 - 10 Jul 2026
From £1277.00 £1021.60
7 nights from £538
Kingfishers
60351 bedroom, dog friendly holiday cottage near Shaftesbury, Dorset.
Great care and attention has been put into this barn conversion, resulting in a truly cosy, yet spacious retreat for couples or solo travellers to enjoy. Located in Gillingham in n...
7 nights from £538
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20% off
29 Jun 2026 - 6 Jul 2026
From £638.00 £510.40
7 nights from £1400
Hood's
60452 bedroom, dog friendly self catering cottage near Bridport, Dorset.
**Hood's can accommodate flexible check in days – please contact us to request.** This stunning barn and milking parlour conversion is set within the glorious Dorset countryside...
7 nights from £1400
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20% off
26 Jun 2026 - 3 Jul 2026
£1750.00 £1400.00
7 nights from £926 *
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 £926 *
British Travel Awards 2025
Best company for UK holiday home rentals
7 nights from £599 *
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 £599 *
7 nights from £599 *
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 £599 *
Whetley Farm
7 nights from £1198
7 nights from £722 *
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 £722 *
7 nights from £902 *
The Old Dairy
55512 bedroom, dog friendly cottage near Wimborne Minster, Dorset.
The Old Dairy is one of the most stunning holidays homes you could visit with curated interior touches at every turn. It’s location for local exploring is particularly good with so...
7 nights from £902 *
7 nights from £578 *
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 £578 *
British Travel Awards 2025
Best company for UK holiday home rentals
With as many opportunities to relax with the kids as there are to explore, you can piece together your own perfect Dorset experience. Book yourself a self-catering haven to return to at the end of the day and leave feeling refreshed and revived.
Summer Holiday Homes in Dorset
What's better than spending your summer holiday in Dorset surrounded by the ones you love most? Spending your summer holiday in Dorset surrounded by the ones you love most in a luxury private retreat. At Classic Cottages, we have a wide range in family-friendly holiday cottages, varied in nature and consistent in quality.
To make sure only the best properties make it onto our books, we personally inspect each one. Equipped with a complete inventory, our cottages provide you with an idyllic home-from-home where you can relax as soon as you open the door. Find one to suit you and your family this summer and browse our selection of 40 available cottages in Dorset now.
