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
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.
Stay in one of our 16 cottages in Dorset for May half term
7 nights from £482
Pound Farm Cottage
40761 bedroom thatched self catering cottage near Sherborne, Dorset.
Pound Farm Cottage is a hidden gem; this listed thatched cottage has been thoughtfully renovated to create a spacious, stylish holiday home, retaining many of the original features...
7 nights from £482
7 nights from £561
The Chalet on the Beach
3351Beach Chalet on the beach sleeping two in Lyme Regis, Dorset.
Imagine a holiday right on the seashore of a very special beach, relaxing on your veranda with a glass of something refreshing, watching the gentle waves at one of the most famous ...
7 nights from £561
Need more time? Reserve any cottage for up to 24 hours before booking.
24hr no commitment reservations
You can reserve your holiday dates on your favourite cottage for up to 24 hours. You might need to check with other guests in your party or simply consider whether this cottage is right for your holiday, either way we’re happy to give you the time to step away and mull over your options before paying a penny.
We’ll send you a reminder to see if you want it or not so you won’t lose out. Take time to think it over, you don’t have to rush your decision. Have a cup of tea and when you’re ready, hit the button to book your holiday and start looking forward to it.
7 nights from £454
The Old School Gables
24902 bedroom dog friendly holiday cottage near Bridport, Dorset.
The pretty Dorset village of Drimpton is set in lovely countryside a short drive inland from the stunning Jurassic Coast. This original school house has been converted into extreme...
7 nights from £454
7 nights from £501
Beehive Cottage
40732 bedroom thatched, dog friendly cottage near Dorchester, Dorset.
Beehive Cottage is a charming and cosy cottage for four, on a quiet lane opposite St Mary's church in the village of Puddletown. The village is surrounded by farmland, Thomas Hardy...
7 nights from £501
7 nights from £506
Cedar Lodge
40142 bedroom, dog friendly holiday cottage near Dorchester, Dorset.
Cedar Lodge is a cosy cottage in a quiet rural location. All on one level, the open plan living-room with kitchen and dining areas creates a very sociable space for a couple or sma...
7 nights from £506
7 nights from £525
Celtic Blessing
22562 bedroom holiday 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 £525
7 nights from £585
Dairyman’s Cottage
20942 bedroom, rural holiday cottage near Shaftesbury, Dorset.
Dairyman’s Cottage is traditional yet contemporary, semi-detached and set on a south-facing terrace. The property has a welcoming feel, with a stunning open plan design downstairs,...
7 nights from £585
7 nights from £588
September Cottage
29482 bedroom self catering cottage near the sea near Weymouth, Dorset.
This comfortable semi-detached family home is on the edge of the countryside, yet only three miles from Weymouth with its sandy beaches and historic quay. A 20 minute walk takes yo...
7 nights from £588
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7 nights from £623
Phoebes House
29242 bedroom, rural self catering cottage near Beaminster, Dorset.
A stunning west Dorset location, amazing rural views and a truly luxurious property, Phoebes House and neighbouring property Lottie's Loft (2565) both hidden gems just a short driv...
7 nights from £623
7 nights from £711
Barbridge Cottage
18052 bedroom, rural holiday cottage near Bridport, Dorset.
Nestling in a picturesque valley a fifteen minute drive from the Jurassic Coast, Barbridge Cottage is close to beaches, walks, fossil hunting, country houses, gardens and lovely pu...
7 nights from £711