Dorset Cottages Available for May Half Term

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

Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.

Stay in one of our 31 cottages in Dorset for May half term

Hood's is a 2 bedroom, dog friendly self catering cottage near Bridport, Dorset.
  • Sleeps 4 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1488

Hood's

6045

2 bedroom, dog friendly self catering cottage near Bridport, Dorset.


This stunning barn and milking parlour conversion is set within the glorious Dorset countryside, offering panoramic views across the Marshwood Vale and beyond. Hoods provides luxur...

  • Sleeps 4 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1488

Loaf is a 1 bedroom, dog friendly self catering cottage near Bridport, Dorset.
  • Sleeps 2
  • Dogs welcome
  • Changeover Fri

7 nights from £770

Loaf

6046

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


Loaf is a gorgeous and sympathetic restoration of an ancient Dorset granary with panoramic views across the Marshwood Vale. Its interiors are straight out of a magazine with design...

  • Sleeps 2
  • Dogs welcome
  • Changeover Fri

7 nights from £770

Hood's and Loaf at Kingsland Farm

  • Sleeps 6 + 2 cots in 2 properties
  • Changeover Fri

7 nights from £2258

Freshfields is a 4 bedroom self catering cottage near Dorchester, Dorset.
  • Sleeps 7 + cot
  • No pets
  • Changeover Fri

7 nights from £1233

Freshfields

5706

4 bedroom self catering cottage near Dorchester, Dorset.


Freshfields is a truly outstanding property in a picturesque Dorset village. Recently renovated throughout, the house provides space and privacy for all the family. Just a short dr...

  • Sleeps 7 + cot
  • No pets
  • Changeover Fri

7 nights from £1233

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

7 nights from £534 *

The Dairy

5682

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


A cosy single-storey cottage, a secret wood and wildflower meadow, all available to you in a location only a short drive of the World Heritage Jurassic Coast, are we tempting you y...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £534 *

The Granary is a 2 bedroom, dog friendly holiday cottage near Beaminster, Dorset.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £534 *

The Granary

5683

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


Tucked away in a rural corner of west Dorset you will find The Granary; a single-storey cottage with a shared two acre woodland and wildflower meadow to while away holiday days in....

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £534 *

Whetley Farm

  • Sleeps 8 + 2 cots in 2 properties
  • Changeover Fri

7 nights from £1067

Bluebells is a 2 bedroom, dog friendly cottage in walking distance of Bridport, Dorset.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £683

Bluebells

5624

2 bedroom, dog friendly cottage in walking distance of Bridport, Dorset.


Tucked away in a quiet location, yet just a stone's throw from bustling Bridport and the Jurassic Coast, you will find Bluebells. Situated at the end of a pretty row of cottages, t...

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

7 nights from £683

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

7 nights from £913

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 £913

Pippins is a 2 bedroom, dog friendly character cottage near Beaminster, Somerset.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £517 *

Pippins

5360

2 bedroom, dog friendly character 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 £517 *

Load 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.