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 29 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 29 available cottages in Dorset now. 

Browse from 29 school summer holiday retreats in Dorset

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

7 nights from £515

1 bedroom, rural holiday cottage near Dorchester, Dorset.


Dorset’s World Heritage Jurassic Coast is close to this comfortably furnished, single-storey, spacious cottage. Set within the grounds of the Owners' home, (who may not be resident...

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

7 nights from £515

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

7 nights from £515

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


The Dairy is another extremely comfortable single-storey cottage in this small and friendly farm development. This property has French windows to its own enclosed outside space – t...

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

7 nights from £515

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

  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £515

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


The Linhay is a tucked away single-storey retreat – an ideal base for exploring the wonderful coastline. The cottage nestles alongside the barns, with a fully enclosed gravel court...

  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £515

View
  • 15% off

    29 Jun 2019 - 6 Jul 2019

    £522.35 £444.00

  • 10% off

    13 Jul 2019 - 20 Jul 2019

    £565.88 £509.29

  • 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 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £597

1 bedroom thatched self catering cottage near Sherborne, Dorset.


Pound Farm Cottage is a hidden gem; this listed thatched cottage has been thoughtfully renovated to create a spacious, stylish holiday home, retaining many of the original features...

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

7 nights from £597

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £728

Beach Chalet on the beach sleeping two in Lyme Regis, Dorset.


Imagine a holiday right on the seashore of a very special beach, relaxing on your veranda with a glass of something refreshing, watching the gentle waves at one of the most famous ...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £728

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £533

2 bedroom dog friendly holiday cottage near Bridport, Dorset.


The pretty Dorset village of Drimpton is set in lovely countryside a short drive inland from the stunning Jurassic Coast. This original school house has been converted into extreme...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £533

View
  • 15% off

    28 Jun 2019 - 5 Jul 2019

    £606.62 £515.62

  • 10% off

    12 Jul 2019 - 19 Jul 2019

    £680.15 £612.13

  • 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

We are Gold accredited with the Green Tourism Business Scheme.

  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £620

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


Beehive Cottage is a charming and cosy cottage for four, on a quiet lane opposite St Mary's church in the village of Puddletown. The village is surrounded by farmland, Thomas Hardy...

  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £620

View
  • 15% off

    28 Jun 2019 - 5 Jul 2019

    £646.91 £549.87

  • 10% off

    12 Jul 2019 - 19 Jul 2019

    £724.85 £652.37

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

7 nights from £631

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 £631

View
  • 15% off

    12 Jul 2019 - 19 Jul 2019

    £893.25 £759.05

  • 15% off

    19 Jul 2019 - 26 Jul 2019

    £977.28 £830.45

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