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 12 cottages in Dorset for May half term

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

7 nights from £430

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 £430

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

7 nights from £505

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 £505

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

7 nights from £531

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 £531

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £598

Ivy Cottage

4122

2 bedroom, dog friendly cottage in Cattistock near Dorchester, Dorset.


Imagine life in a tranquil Dorset village and Ivy Cottage is just the sort of place you may picture in your mind. Set in the midst of an Area of Outstanding Natural Beauty, the cot...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £598

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

7 nights from £631

The Old Dairy

4740

2 bedroom, dog friendly former milking parlour near Blandford Forum, Dorset.


This former milking parlour that served the local farm has been beautifully converted into a fabulous holiday home. Situated in a picturesque Dorset village that is full of charact...

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

7 nights from £631

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £674

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 £674

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

7 nights from £721

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 £721

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

7 nights from £725

Dairyman’s Cottage

2094

2 bedroom, rural holiday cottage near Shaftesbury, Dorset.


Located in an Area of Outstanding Natural Beauty, Hatts Farm is a working farm set in 150 acres on the picturesque Dorset and Wiltshire border. Dairyman's Cottage is a traditio...

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

7 nights from £725

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

7 nights from £875

Halcyon Cottage

4693

3 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 £875

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