Cottages for the Summer Holidays in Dorset

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 25 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.  

Summer Holiday Homes in Dorset

What's better than spending your summer holiday in Dorset surrounded by the ones you love most? Spending your 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 25 available cottages in Dorset now. 

Browse from 25 summer holiday retreats in Dorset

  • Sleeps 3 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £610

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


A gorgeous, chocolate-box cottage that is the ideal escape, nestled in the heart of one of Dorset's picturesque villages. Just a stone's throw from the lovely local pub, Wayside Co...

  • Sleeps 3 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £610

  • Sleeps 6
  • Dogs welcome
  • Changeover Sat

7 nights from £1288

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


This beautiful, historical Grade II Listed semi-detached property oozes charm and luxury. Built in 1607, Oak House is one of the oldest houses in Yetminster and its dated enriched ...

  • Sleeps 6
  • Dogs welcome
  • Changeover Sat

7 nights from £1288

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

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

7 nights from £753

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 £753

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £665

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


Imagine life in a tranquil Dorset village and Ivy Cottage is just the sort of place you may picture in your mind. Set in the midst of an Area of Outstanding Natural Beauty, the cot...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £665

  • Sleeps 10 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £2022

5 bedroom, dog friendly cottage near the beach near Lyme Regis.


Less than half a mile from the World Heritage Jurassic Coast, The Old Manor House is a beautiful 16th Century, Grade II Listed house, full of character with a delightful enclosed g...

  • Sleeps 10 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £2022

  • 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 on a quiet lane opposite St Mary's church in the village of Puddletown. Surrounded by farmland, the pretty village is nestled in the ...

  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £620

  • 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 12 + 2 cots
  • Dogs welcome
  • Changeover Thu

7 nights from £2081

6 bedroom thatched, dog friendly home near Lyme Regis, South Devon.


Buddlewall is an historic east Devon farmhouse, in a beautiful hidden rural setting, a short drive inland from the spectacular World Heritage east Devon and Dorset Jurassic Coast. ...

  • Sleeps 12 + 2 cots
  • Dogs welcome
  • Changeover Thu

7 nights from £2081

Readymade beds and fluffy towels; this simple but appreciated welcome is standard with us.

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £627

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 create a very sociable space for a couple or smal...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £627

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £766

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 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £766

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