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 27 luxury retreats available for you to choose from. Find your favourite now.

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 27 available cottages in Dorset now. 

Browse from 27 school summer holiday retreats in Dorset

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


Converted from a former stable, Brookland Barn offers an immaculate property all on one level in fabulous surroundings. The south-facing barn looks out over the enclosed garden and...

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

Price per week £910 - £1070

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  • 15% off

    3 Aug 2018 - 10 Aug 2018

    £1070.00 £909.50

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


With stunning rural views from your deck, and a fabulous open plan interior, Furrow Lodge snuggles into the hillside in the delightful Dorset countryside and offers a real opportun...

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

Price per week £917 - £975

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


Lynchet Lodge is a gorgeous open plan cottage, beautifully furnished and equipped to provide all that you need for a relaxing holiday in rural Dorset. The open plan kitchen/dining/...

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

Price per week £917 - £975

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

Price per week £1060 - £1191

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

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

Price per week £956 - £1195

View
  • 20% off

    3 Aug 2018 - 10 Aug 2018

    £1195.00 £956.00

3 bedroom self catering cottage in Wareham, Dorset.


Wareham is the gateway to the Jurassic Coast, a fabulous base from which to explore the Isle of Purbeck. Just within the ancient Saxon walls of this historic market town, Northgate...

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

Price per week £975 - £995

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

Price per week £1114 - £1375

Dog friendly safari tent glamping for six near Shaftesbury, Dorset.


Glamping at Black Pig Retreats allows you to escape the everyday and enjoy a fabulous holiday with a difference, where you can cook with fire, collect logs, listen to birdsong and ...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £1135 - £1275

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 (1 only)
  • Changeover Fri

Price per week £1184 - £1260

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


This tranquil and elegant period farmhouse has a luxurious contemporary interior, spacious flexible accommodation and a beautiful enclosed garden. The glorious west Dorset location...

  • Sleeps 8
  • Dogs welcome
  • Changeover Fri

Price per week £2141 - £2185

25% off for parties up to 4 between 1 Sep and 29 Sep 2018. Bedrooms 3 and 4 are excluded at the discounted rate.

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

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