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 24 cottages in Dorset for May half term

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

7 nights from £732

2 bedroom self catering cottage near the sea near Weymouth, Dorset.


This comfortable semi-detached family home is on the edge of the countryside, yet only three miles from Weymouth with its sandy beaches and historic quay. A 20 minute walk takes yo...

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

7 nights from £732

View
  • 15% off

    21 Dec 2018 - 28 Dec 2018

    £744.51 £633.25

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

7 nights from £783

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


This pretty detached former coach house is in beautiful rural Dorset within easy reach of the stunning World Heritage Jurassic coastline. The Old Coach House has a spacious brig...

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

7 nights from £783

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

7 nights from £941

2 bedroom, rural holiday cottage near Bridport, Dorset.


Nestling in a picturesque valley a fifteen minute drive from the Jurassic Coast, Barbridge Cottage is close to beaches, walks, fossil hunting, country houses, gardens and lovely pu...

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

7 nights from £941

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

7 nights from £664

3 bedroom holiday cottage near Bridport, Dorset.


This sunny south-facing cottage enjoys a quiet rural position on the edge of the beautiful village of Netherbury, a short drive from the beaches and cliffs of the World Heritage Ju...

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

7 nights from £664

Our guests rate us 4.8/5 on Feefo, the independent review site.

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

7 nights from £786

2 bedroom, rural cottage near the beach near Bridport, Dorset.


The Parlour is an excellent choice for a family, with French windows opening out onto an enclosed gravelled patio, comfortable accommodation for five guests – one of the three sing...

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

7 nights from £786

View
  • 20% off

    21 Dec 2018 - 28 Dec 2018

    £796.00 £636.80

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

7 nights from £938

2 bedroom, rural holiday cottage near Shaftesbury, Dorset.


Semi-detached Hatts Barn is a contemporary, reversed level barn conversion on a wide south-facing terrace. The large en suite master bedroom and a twin bedded family room (the beds...

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

7 nights from £938

View
  • 25% off

    21 Dec 2018 - 28 Dec 2018

    £926.12 £694.50

  • 20% off

    28 Dec 2018 - 4 Jan 2019

    £926.12 £740.80

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1002

3 bedroom thatched, dog friendly cottage in Tolpuddle, Dorset.


This very pretty thatched cottage is in the tranquil historic village of Tolpuddle, surrounded by beautiful countryside and just 15 miles from the World Heritage Jurassic Coast. Wi...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1002

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

7 nights from £1051

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


This is an excellent base for exploring rural and coastal Dorset. Cranborne Chase (an Area of Outstanding Natural Beauty) is on the doorstep, and the beaches of the Jurassic Coast ...

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

7 nights from £1051

  • Sleeps 6 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1074

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


Barn Owls Cottage, a semi-detached cottage converted from an 18th Century stone barn, has retained much of its original character with inset fossils and huge oak beams. The kitchen...

  • Sleeps 6 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1074

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

7 nights from £1080

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


This beautiful barn conversion at the heart of a working dairy farm is just inland from Dorset's spectacular Jurassic Coast and its beaches. The rural setting will please all the f...

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

7 nights from £1080

Choose from our exclusive collection at the best prices with real time availability.

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