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 15 cottages in Dorset for May half term

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £637

Hatts Barn

2093

2 bedroom, rural holiday cottage near Shaftesbury, Dorset.


Hatts Farm is a working farm set in 150 acres on the Dorset and Wiltshire border, located in an Area of Outstanding Natural Beauty. The semi-detached Hatts Barn is a contemporary, ...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £637

  • Sleeps 6 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £795

Meadows Barn

4293

3 bedroom self catering cottage near Yeovil, Dorset.


Meadows Barn is on the edge of the tranquil Dorset village of Halstock, with far reaching views over the surrounding countryside, ideal for a family holiday or a great base for fri...

  • Sleeps 6 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £795

  • Sleeps 6
  • Dogs welcome
  • Changeover Sat

7 nights from £1119

Oak House

4438

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


This beautiful, historical Grade II Listed semi-detached property oozes charm and luxury. Built in 1607, Oak House is one of the oldest houses in Yetminster and its dated enriched ...

  • Sleeps 6
  • Dogs welcome
  • Changeover Sat

7 nights from £1119

  • Sleeps 12 + 2 cots
  • Dogs welcome
  • Changeover Thu

7 nights from £1839

Buddlewall

3979

6 bedroom thatched, dog friendly home near Lyme Regis, South Devon.


Buddlewall is an historic east Devon farmhouse, in a beautiful hidden rural setting, a short drive inland from the spectacular World Heritage east Devon and Dorset Jurassic Coast. ...

  • Sleeps 12 + 2 cots
  • Dogs welcome
  • Changeover Thu

7 nights from £1839

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

Hatts Farm

  • Sleeps 9 + 2 cots in 2 properties
  • Changeover Fri

7 nights from £1234