Dorset Boltholes Available in May

Spring is well under way, the sun is shining and Dorset is looking particularly radiant. Make the most of this special time of year and treat yourself to a stay in a luxury self-catering cottage. Our collection of 13 Dorset cottages available in May have all been handpicked; personally inspected and fully equipped to ensure your stay is the best it can be.Read more

If you want to make your May half-term count this year, why not book a family holiday in Dorset? Our range of self-catering cottages come in all shapes and sizes, with plenty of room for your little ones. Many cottages have extra facilities like swimming pools, games rooms and large gardens so the kids will be in entertainment heaven while mum and dad relax. 

May isn't all about half-term though. There are two bank holidays to look forward to, and lots of opportunities to make the most of this beautiful and diverse county ahead of the summer crowds. Whether you're looking for a solo retreat, romantic couples getaway or catch up with friends, we can help you find the ideal cottage for you. If you've got a four-legged member of the family, it's great news as many of our cottages are dog-friendly too.

Dorset Cottages for May Half-Term

With its dramatic coastline, rolling countryside alive with colour and patchwork of towns and villages, Dorset provides a wonderful destination to explore, whether it's for the first time or the fifteenth. Book your Classic cottage today and be sure to receive excellent customer service with the finest quality self-catering accommodation.  

Choose from 13 available self-catering cottages in Dorset

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £410

The Linhay

2661

1 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...

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £410

  • Sleeps 2
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £720

Toby's Hut

4723

1 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...

  • Sleeps 2
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £720

Need more time? Reserve any cottage for up to 24 hours before booking.

  • Sleeps 2
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £845

La Cabine Francaise

4726

1 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...

  • Sleeps 2
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £845

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £580

Celtic Blessing

2256

2 bedroom 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...

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £580

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £606

Tolpuddle Cottage

3752

3 bedroom thatched, dog friendly cottage in Tolpuddle, Dorset.


This pretty thatched cottage is in the tranquil historic village of Tolpuddle, just 15 miles from the World Heritage Jurassic Coast. An ideal base for a family holiday or perfect f...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £606

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Mon

7 nights from £648

Rectory Cottage

4795

2 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 in to the driveway you will lov...

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Mon

7 nights from £648

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £657

No 1 By The Sea

4965

2 bedroom holiday apartment near the beach near Weymouth, Dorset.


Just a short stroll from the sea, this super-stylish apartment is a gorgeous retreat with an added touch of luxury. Situated on the ground floor of a smart, modern apartment buildi...

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £657

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £795

Halcyon Cottage

4693

2 bedroom cottage near the beach and Lulworth Cove near Dorchester, Dorset.


Less than two miles from Lulworth Cove, part of the only World Heritage Site in England, Halcyon Cottage is a pretty, detached stone cottage in the heart of the village of West Lul...

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £795

Choose from our exclusive collection at the best prices with real time availability.

  • Sleeps 5 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £756

Park Farm Byre

4956

3 bedroom, dog friendly holiday cottage with hot tub near Dorchester, Dorset.


Tucked away in a rural location, you will find Park Farm Byre, a stylish retreat complete with wood-fired hot tub. All on one level (apart from two steps from the sitting-room to t...

  • Sleeps 5 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £756

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £690

Crosskeys Cottage

4855

3 bedroom, dog friendly holiday cottage near Beaminster, Dorset.


Situated in the pretty west Dorset village of Broadwindsor, surrounded by countryside and not far from the coast, Crosskeys Cottage is a wonderful place to spend your holiday. Buil...

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £690

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