Dorset Boltholes Available in May

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 51 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 51 available self-catering cottages in Dorset

The Old Dairy is a 2 bedroom, dog friendly cottage near Wimborne Minster, Dorset.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £864

The Old Dairy

5551

2 bedroom, dog friendly cottage near Wimborne Minster, Dorset.


Situated within the southern neolithic ring of Knowlton Church and Earthworks and perfectly positioned under a Dark Sky Reserve, is The Old Dairy; a stylish and modern conversion t...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £864

The Gardens is a 2 bedroom, dog friendly self catering cottage in Sherborne, Dorset.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £598

The Gardens

5406

2 bedroom, dog friendly self catering cottage in Sherborne, Dorset.


From the rolling hills of the Dorset countryside to the beautiful historic streets of Sherborne and down to the Jurassic Coast, explore it all whilst staying at The Gardens. This c...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £598

Pippins is a 3 bedroom, dog friendly holiday cottage near Beaminster, Somerset.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £577

Pippins

5360

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


Pippins is a picture postcard country cottage nestled in the charming Somerset village of North Perrott - not far from the Dorset border. This cosy home can cater for all of the fa...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £577

Seymour Barn is a 2 bedroom, dog friendly self catering cottage in Bridport, Dorset.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £931

Seymour Barn

5314

2 bedroom, dog friendly self catering cottage 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...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £931

Periwinkle Cottage is a 1 bedroom, dog friendly self catering cottage in Bridport, Dorset.
  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £451

Periwinkle Cottage

5258

1 bedroom, dog friendly self catering cottage in Bridport, Dorset.


Tucked away off one of Bridport's vibrant streets is Periwinkle Cottage, a beautiful home ready to welcome you for a fantastic stay. This gorgeous terraced retreat is the perfect p...

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

7 nights from £451

Ginny's Barn is a 2 bedroom, self catering cottage near Bridport, Dorset.
  • Sleeps 3
  • No pets
  • Changeover Fri

7 nights from £598

Ginny's Barn

5276

2 bedroom, self catering cottage near Bridport, Dorset.


Find your 'Far from the Madding Crowd' moment in the beautiful west Dorset countryside with a stay at Ginny's Barn. This quaint cottage is set in the grounds of the owners' home an...

  • Sleeps 3
  • No pets
  • Changeover Fri

7 nights from £598

Quince Cottage is a 3 bedroom, dog friendly cottage close to the beach near Bridport, Dorset.
  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £762

Quince Cottage

5190

3 bedroom, dog friendly cottage close to the beach near Bridport, Dorset.


With the World Heritage Jurassic Coast within one mile's walk, Quince Cottage is a welcoming home in the pretty West Dorset village of Chideock. This charming home is the perfect l...

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £762

Woodville Cottage is a 3 bedroom, dog friendly home near the beach in Lyme Regis.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Wed

7 nights from £995

Woodville Cottage

5151

3 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...

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Wed

7 nights from £995

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

St Peter's Cottage is a 3 bedroom thatched, dog friendly cottage near Dorchester, Dorset.
  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1037

St Peter's Cottage

5135

3 bedroom thatched, dog friendly cottage near Dorchester, Dorset.


Dating back to the early 17th Century, this picture perfect, Grade II Listed thatched cottage sits in the heart of a rural Dorset village. Recently renovated by the owners, St Pete...

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

7 nights from £1037

Park Farm Byre is a 3 bedroom, dog friendly holiday cottage near Dorchester, Dorset.
  • Sleeps 5 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £644

Park Farm Byre

4956

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


Tucked away in a rural location, you will find Park Farm Byre, a stylish retreat complete with hot tub and perfectly situated on a number of country and woodland walks. All on one ...

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

7 nights from £644

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