Dorset Cottages Available for May Half Term
With temperatures warming, long daylight hours and a dazzling sun in the sky, it can mean only one thing: summer is coming. Make the most of your May half term and head to Dorset to luxuriate in your own private self-catering cottage. Gather your troops, pack your bags and hop in the car; the holiday of a lifetime is ready and waiting. Read more
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.Stay in one of our 30 cottages in Dorset for May half term
7 nights from £2330
Oak Tree House
61124 bedroom, dog friendly holiday cottage near Dorchester, Dorset.
Oak Tree House is a particularly special property for gathering friends and family (plus the four-legged variety) together. Set in stunning grounds in the little village of Frampto...
7 nights from £2330
7 nights from £571
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 £571
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20% off
8 Jun 2026 - 15 Jun 2026
£605.00 £484.00
7 nights from £1488
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 £1488
7 nights from £770
Loaf At The Granary
60461 bedroom, dog friendly self catering cottage near Bridport, Dorset.
**Loaf At The Granary can accommodate flexible check in days – please contact us to request.** Loaf At The Granary is a gorgeous and sympathetic restoration of an ancient Dorset...
7 nights from £770
British Travel Awards 2025
Best company for UK holiday home rentals
Hood's and Loaf at Kingsland Farm
7 nights from £2258
7 nights from £1343
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 £1343
7 nights from £516 *
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 £516 *
7 nights from £534 *
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 £534 *
Whetley Farm
7 nights from £1050
7 nights from £731 *
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 £731 *
We’re here to help you find your perfect place to stay 7 days a week.
Open 7 days a week
Call our office on 01326 555555, email hello@classic.co.uk or click on the live chat button in the bottom right of the screen to talk directly to someone who can help with choosing your holiday. If you have any questions or need a hand with the booking process, we’re happy to help.
After booking your holiday with us, you’ll receive your holiday details two weeks before your holiday. This also includes our emergency out of hours phone number for when the office is closed, so we’re never more than a phone call away!
If you've got children in tow, why not book yourselves into a luxury self-catering cottage this May half term? From babies to young children to teenagers, our portfolio includes properties of a wide variety and consistent quality. Pick a cottage with a private swimming pool, or find one with a games room; kids will find plenty to entertain themselves with whilst mum and dad sit back and relax.
However you want to plan your dream retreat, we'll help you to find your perfect place. From one-bed cottages for solo retreats to big family-friendly home-from-homes, let your imagination soar as you pour through our selection of available cottages in Dorset.
Cottages for May Half Term in Dorset
At Classic Cottages we pride ourselves on marketing only the finest quality self-catering cottages in Dorset. All of our cottages are personally inspected to meet exacting standards; carefully selected and fully equipped so that you can spend the holiday of a lifetime without worrying about a thing.
