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 37 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 37 available cottages in Dorset now. 

Browse from 37 school summer holiday retreats in Dorset

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 Owner’s home, The Stables is self-cont...

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

Price per week £515 - £725

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
  • Regret no pets
  • Changeover Sat

Price per week £515 - £592

We are Gold accredited with the Green Tourism Business Scheme.

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

Price per week £515 - £592

1 bedroom, dog friendly self catering cottage near Sherborne, Dorset.


This cosy, compact yet delightful bolthole for two is set in a wonderfully tranquil hamlet in north Dorset with village shops and a choice of two pubs within two miles. Built in lo...

  • Sleeps 2
  • Dogs welcome (1 only)
  • Changeover Fri

Price per week £519 - £597

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


Badgers Cottage, a snug semi-detached cottage for two, is set in a farmyard, beautifully converted from an 18th Century stone barn. All on one level, the open plan design gives a w...

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £528 - £607

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

Price per week £586 - £674

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

Price per week £597 - £765

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

Price per week £728 - £837

Arrive at your handpicked holiday home safe in the knowledge it’s been fully inspected.

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

Price per week £533 - £750

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


Cedar Lodge is a cosy cottage in a quiet rural location. All on one level, the open plan living-room with kitchen and dining areas creates a very sociable space for a couple or sma...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £620 - £795

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