Cottages for the Summer Holidays in Dorset

Cottages for the Summer Holidays in Dorset

Our self-catering holiday cottages come in all shapes and sizes for the school summer holidays. 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.

We currently have 49 cottages available for you to choose from. Find your favourite now.Read more

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 49 available cottages in Dorset now. 

Browse from 49 summer holiday cottages in Dorset

West Hembury Farm

  • Sleeps 8 + 2 cots in 2 properties
  • Changeover Fri

7 nights from £1650

Badgers Cottage is a 1 bedroom, dog friendly cottage near Bridport, Dorset.
  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £633

Badgers Cottage

3014

1 bedroom, dog friendly cottage near Bridport, Dorset.


This pretty semi-detached cottage for two is nestled within an Area of Outstanding Natural Beauty on West Hembury Farm. Badgers Cottage is an 18th Century stone barn that has be...

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £633

We’re here to help you find your perfect place to stay 7 days a week.

Barn Owls Cottage is a 3 bedroom, dog friendly cottage near Bridport, Dorset.
  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1017

Barn Owls Cottage

3015

3 bedroom, dog friendly cottage near Bridport, Dorset.


Barn Owls Cottage is a semi-detached cottage that has been converted from an 18th Century stone barn. Despite having stylish modern fittings, it has still retained much of its orig...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1017

Owl's Nest Cottage is a 1 bedroom, dog friendly cottage near Sherborne, Dorset.
  • Sleeps 2
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £580

Owl's Nest Cottage

2942

1 bedroom, dog friendly cottage near Sherborne, Dorset.


This cosy, compact, 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

7 nights from £580

Beech Cottage is a 5 bedroom, dog friendly cottage with views over the nature reserve near Bridport, Dorset.
  • Sleeps 9 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1571

Beech Cottage

2887

5 bedroom, dog friendly cottage with views over the nature reserve near Bridport, Dorset.


This beautiful stone farmhouse has something very special indeed - it comes with a 450 acre nature reserve and a unique relationship with Dorset Wildlife Trust, offering comfortabl...

  • Sleeps 9 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1571

Sturthill Stable is a 3 bedroom, dog friendly barn conversion set within a working farm near Bridport, Dorset.
  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £940

Sturthill Stable

2829

3 bedroom, dog friendly barn conversion set within a working farm 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 £940

The Linhay is a 1 bedroom cottage near the beach near Bridport, Dorset.
  • Sleeps 2 + cot
  • No pets
  • Changeover Sat

7 nights from £575

The Linhay

2661

1 bedroom cottage near the beach near Bridport, Dorset.


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

  • Sleeps 2 + cot
  • No pets
  • Changeover Sat

7 nights from £575

The Parlour is a 2 bedroom cottage with views of Golden Cap near Bridport, Dorset
  • Sleeps 5 + cot
  • No pets
  • Changeover Sat

7 nights from £794

The Parlour

2662

2 bedroom cottage with views of Golden Cap near Bridport, Dorset


The Parlour is an excellent choice for a family, with French doors opening out onto an enclosed gravelled patio, comfortable accommodation for five guests – one of the three single...

  • Sleeps 5 + cot
  • No pets
  • Changeover Sat

7 nights from £794

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

The Dairy is a 1 bedroom cottage close to the Jurassic Coast, near Bridport, Dorset.
  • Sleeps 2 + cot
  • No pets
  • Changeover Sat

7 nights from £610

The Dairy

2663

1 bedroom cottage close to the Jurassic Coast, near Bridport, Dorset.


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

  • Sleeps 2 + cot
  • No pets
  • Changeover Sat

7 nights from £610

Doghouse Farm

  • Sleeps 9 + 3 cots in 3 properties
  • Changeover Sat

7 nights from £1978

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