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 33 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 33 available self-catering cottages in Dorset

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

7 nights from £393

The Linhay

2661

1 bedroom 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 £393

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

7 nights from £397

Owl's Nest Cottage

2942

1 bedroom, dog friendly self catering cottage near Sherborne, Dorset.


This cosy, compact, delightful bolthole for two is set in a wonderfully tranquil hamlet in north Dorset with village shops and a choice of two pubs within two miles. Built in lo...

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

7 nights from £397

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

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

7 nights from £403

The Stables

1965

1 bedroom, rural holiday cottage near Dorchester, Dorset.


Dorset’s World Heritage Jurassic Coast is close to this comfortably furnished, single-storey, spacious cottage. Set within the grounds of the owner’s home, The Stables is self-cont...

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

7 nights from £403

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £437

Pound Farm Cottage

4076

1 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...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £437

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £547

The Chalet on the Beach

3351

Cabin 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 ...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £547

  • Sleeps 3 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £438

Wayside Cottage

4484

2 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...

  • Sleeps 3 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £438

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £417

The Old School Gables

2490

2 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...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £417

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

7 nights from £434

Old Sandpitts Cottage

4504

2 bedroom thatched self catering cottage near Bridport, Dorset.


Tucked away down its own private track, this picture-perfect thatched cottage is a little gem. Surrounded by its own private garden, the cottage is very peaceful and offers space f...

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

7 nights from £434

Readymade beds and fluffy towels; this simple but appreciated welcome is standard with us.

  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £453

Beehive Cottage

4073

2 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 ...

  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £453

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £459

Cedar Lodge

4014

2 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 create a very sociable space for a couple or smal...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £459

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