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 18 cottages in Dorset for May half term
Spring View Cottages
7 nights from £1172
7 nights from £433
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 £433
7 nights from £679
The Lookout
57632 bedroom, dog friendly apartment with sea views, near Studland.
In an elevated position with views out to Swanage Bay, The Lookout is a modern, stylish, first floor apartment for up to four lucky guests and their four-legged friend to enjoy. Ta...
7 nights from £679
7 nights from £739
Spring View
56863 bedroom rural cottage near the sea and close to Dorchester, Dorset.
A family friendly holiday home situated in a beautiful rural Dorset hamlet with countryside views galore. Recently renovated throughout, Spring View, offers a peaceful escape from ...
7 nights from £739
7 nights from £593
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 £593
7 nights from £663
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 £663
7 nights from £989
Seymour Barn
53142 bedroom, dog friendly barn conversion in Bridport, Dorset.
With the bustling market town of Bridport within striking distance, this beautiful barn conversion is the perfect home-away-from-home. A delightful spot to explore all the beauty a...
7 nights from £989
7 nights from £925
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 £925
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 £820
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 £820
7 nights from £686
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 £686
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.
