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 £430
The Linhay
26611 bedroom, dog friendly 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 £430
7 nights from £430
The Dairy
26631 bedroom cottage near 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 £430
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 £720
Toby's Hut
47231 bedroom, dog friendly shepherds hut near Lyme Regis, Dorset.
Located in the west Dorset Area of Outstanding Natural Beauty and just a 15 minute drive from fabulous Lyme Regis, Toby's Hut is a bespoke Shepherd's Hut, sitting in a perfect spot...
7 nights from £720
7 nights from £845
La Cabine Francaise
47261 bedroom, dog friendly Shepherds Hut near Dorchester, Dorset.
Welcome to La Cabine Francaise, a glorious expanse of glamping bliss with a French twist. Set in the stunning Dorset countryside, this exclusive spot for two provides the perfect r...
7 nights from £845
7 nights from £505
Wayside Cottage
44842 bedroom thatched, dog friendly cottage near Beaminster, Dorset.
A gorgeous, chocolate-box cottage that is the ideal escape, nestled in the heart of one of Dorset's picturesque villages. Just a stone's throw from the lovely local pub, Wayside Co...
7 nights from £505
7 nights from £478
The Old School Gables
24902 bedroom dog friendly cottage near the market town of 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 £478
7 nights from £527
Beehive Cottage
40732 bedroom thatched, dog friendly cottage near Dorchester, Dorset.
Beehive Cottage is a charming and cosy cottage on a quiet lane opposite St Mary's church in the village of Puddletown. Surrounded by farmland, the pretty village is nestled in the ...
7 nights from £527
7 nights from £531
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 £531
Our property managers are local experts who handpick perfect places to stay.
Local experts
We scour the coast and country to winkle out bits worth sharing with you, the best properties in lovely locations. While we’re out and about, we gather together the best things to do so that you can start planning your holiday as soon as you’ve booked.
The ‘Explore Nearby’ tab on our cottage pages show what’s nearby along with relevant articles from our holiday guides from Notes and Stories, where you’ll find hand-written experiences of outings across the South and West, from dog-friendly pubs on the Isle of Wight to free things to do in south Devon and everything in between.
7 nights from £598
Ivy Cottage
41222 bedroom, dog friendly holiday cottage in Cattistock near Dorchester, Dorset.
Imagine life in a tranquil Dorset village and Ivy Cottage is just the sort of place you may picture in your mind. Set in the midst of an Area of Outstanding Natural Beauty, the cot...
7 nights from £598
7 nights from £631
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 £631