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 33 cottages 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 33 available cottages in Dorset now. 

Browse from 33 summer holiday cottages in Dorset

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

7 nights from £843

No 1 By The Sea

4965

2 bedroom holiday apartment near the beach near Weymouth, Dorset.


Just a short stroll from the sea, this super-stylish apartment is a gorgeous retreat with an added touch of luxury. Situated on the ground floor of a smart, modern apartment buildi...

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

7 nights from £843

  • Sleeps 5 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1031

Park Farm Byre

4956

3 bedroom, dog friendly holiday cottage with hot tub near Dorchester, Dorset.


Tucked away in a rural location, you will find Park Farm Byre, a stylish retreat complete with hot tub and a paddock perfect for the children and the family dog to run off steam. A...

  • Sleeps 5 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1031

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

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £885

Crosskeys Cottage

4855

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


Situated in the pretty west Dorset village of Broadwindsor, surrounded by countryside and not far from the coast, Crosskeys Cottage is a wonderful place to spend your holiday. Buil...

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £885

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £893

Bay Tree Cottage

4835

3 bedroom, dog friendly cottage near Bridport, Dorset.


Situated in a sleepy west Dorset village, just a short drive from the spectacular Jurassic Coast, you will find this pretty terraced cottage. Recently renovated, Bay Tree Cottage o...

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £893

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

7 nights from £831

Rectory Cottage

4795

2 bedroom cottage near Bridport, Dorset


Hidden away in the grounds of a Grade II Listed former rectory, this picture-perfect cottage is a delightful Dorset escape. From the moment you pull in to the driveway you will lov...

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

7 nights from £831

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

7 nights from £728

The Old Dairy

4740

2 bedroom, dog friendly former milking parlour near Blandford Forum, Dorset.


This former milking parlour that served the local farm has been beautifully converted into a fabulous holiday home. Situated in a picturesque Dorset village that is full of charact...

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

7 nights from £728

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £832

Fox Cottage

4712

1 bedroom stylish cottage in Beaminster, Dorset.


Tucked away in an oh-so-pretty part of historic Beaminster, Fox Cottage is a gorgeous retreat for two. As soon as you arrive at this picture-perfect terraced cottage, you will want...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £832

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

7 nights from £720

Toby's Hut

4723

1 bedroom, dog friendly shepherds hut near Lyme Regis, Dorset.


Located in the west Dorset Area of Outstanding Natural Beauty and just a 15 minute drive from fabulous Lyme Regis, Toby's Hut is a bespoke Shepherd's Hut, sitting in a perfect spot...

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

7 nights from £720

We are Gold accredited with the Green Tourism Business Scheme.

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

From £160 per night

La Cabine Francaise

4726

1 bedroom, dog friendly Shepherds Hut near Dorchester, Dorset.


Welcome to La Cabine Francaise, a glorious expanse of glamping bliss with a French twist. Set in the stunning Dorset countryside, this exclusive spot for two provides the perfect r...

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

From £160 per night

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

7 nights from £1109

Halcyon Cottage

4693

2 bedroom cottage near the beach and Lulworth Cove near Dorchester, Dorset.


Less than two miles from Lulworth Cove, part of the only World Heritage Site in England, Halcyon Cottage is a pretty, detached stone cottage in the heart of the village of West Lul...

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

7 nights from £1109

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