Cottages for the School Summer Holidays in Dorset

Take the children on holiday or invite the whole family along for a slice of summer action. Our self-catering holiday cottages come in all shapes and sizes for the school summer holidays. Pick your favourite now and get ready to make magical memories. We currently have 12 luxury retreats available for you to choose from. Find your favourite now.Read more

Hunt for fossils along the stunning Jurassic Coast, tuck into a delicious afternoon tea in a cool cafe sourced with local goods, stroll along the coast path or head inland and take up one of the many cycling routes, the choices are boundless. With as many opportunities to relax with the kids as there are to explore, you can piece together your own perfect Dorset experience. Book yourself a self-catering haven to return to at the end of the day and leave feeling refreshed and revived.  

School Summer Holiday Homes in Dorset

What's better than spending your school summer holiday in Dorset surrounded by the ones you love most? Spending your school summer holiday in Dorset surrounded by the ones you love most in a luxury private retreat. At Classic Cottages, we have a wide range in family-friendly holiday cottages, varied in nature and consistent in quality.

To make sure only the best properties make it onto our books, we personally inspect each one. Equipped with a complete inventory, our cottages provide you with an idyllic home-from-home where you can relax as soon as you open the door. Find one to suit you and your family this summer and browse our selection of 12 available cottages in Dorset now. 

Browse from 12 school summer holiday retreats in Dorset

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £586

1 bedroom, rural holiday cottage near Beaminster, Dorset.


Lottie’s Loft is a luxurious first floor barn conversion, a gorgeous bolthole surrounded by beautiful Dorset countryside. Exterior steps lead from the decking to a balcony with bes...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £586

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

7 nights from £608

2 bedroom, rural holiday cottage near Shaftesbury, Dorset.


Dairyman’s Cottage is traditional yet contemporary, semi-detached and set on a south-facing terrace. The property has a welcoming feel, with a stunning open plan design downstairs,...

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

7 nights from £608

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

  • Sleeps 4
  • Regret no pets
  • Changeover Fri

7 nights from £677

2 bedroom, rural self catering cottage near Beaminster, Dorset.


A stunning west Dorset location, amazing rural views and a truly luxurious property, Phoebes House and neighbouring property Lottie's Loft (2565) both hidden gems just a short driv...

  • Sleeps 4
  • Regret no pets
  • Changeover Fri

7 nights from £677

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

7 nights from £692

3 bedroom self catering cottage in rural 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 £692

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  • 20% off

    27 Dec 2019 - 3 Jan 2020

    £1081.12 £864.90

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

7 nights from £808

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 £808

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

7 nights from £756

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 twin...

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

7 nights from £756

View
  • 20% off

    20 Dec 2019 - 27 Dec 2019

    £944.72 £755.78

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £768

3 bedroom thatched self catering cottage near Bridport, Dorset.


This very attractive thatched, detached property is in a tucked away rural setting in unspoilt west Dorset. Old Sandpitts Lodge is a very easy short drive inland from the fabulous ...

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £768

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

7 nights from £846

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 £846

Each and every one of our cottages is fully equipped with everything you’ll need on holiday.

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

7 nights from £870

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 £870

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £913

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 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £913

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