Dorset Retreats for October Half Term

Dorset Retreats for October Half Term

Watch summer fade into autumn from the comfort of a self-catering cottage in Dorset. We  have a wide range of cottages peppered across Dorset of all different shapes and sizes available for an unforgettable autumn. Spend your days exploring Dorset from country to coast, treading golden leaves and breathing crisp air, and then when you're ready return to your home-from-home together.  Read more

Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.

35 self-catering cottages for October half term in Dorset

Lavender Cottage is a 2 bedroom, dog friendly cottage near the beach in Christchurch.
  • Sleeps 4 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £702 * booking fees included

Lavender Cottage

6176

2 bedroom, dog friendly cottage near the beach in Christchurch.


Lavender Cottage is a delightful two bedroom home with open plan living areas and wonderful outdoor space. Set in the exclusive Wick Village it is just a short walk from one of Dor...

  • Sleeps 4 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £702 *

Freshfields is a 4 bedroom self catering cottage near Dorchester, Dorset.
  • Sleeps 7 + cot
  • No pets
  • Changeover Fri

7 nights from £888 * booking fees included

Freshfields

5706

4 bedroom self catering cottage near Dorchester, Dorset.


Freshfields is a truly outstanding property in a picturesque Dorset village. Recently renovated throughout, the house provides space and privacy for all the family. Just a short dr...

  • Sleeps 7 + cot
  • No pets
  • Changeover Fri

7 nights from £888 *

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Bluebells is a 2 bedroom, dog friendly cottage in walking distance of Bridport, Dorset.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £598 * booking fees included

Bluebells

5624

2 bedroom, dog friendly cottage in walking distance of Bridport, Dorset.


Tucked away in a quiet location, yet just a stone's throw from bustling Bridport and the Jurassic Coast, you will find Bluebells. Situated at the end of a pretty row of cottages, t...

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

7 nights from £598 *

The Old Dairy is a 2 bedroom, dog friendly cottage near Wimborne Minster, Dorset.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £730 * booking fees included

The Old Dairy

5551

2 bedroom, dog friendly cottage near Wimborne Minster, Dorset.


The Old Dairy is one of the most stunning holidays homes you could visit with curated interior touches at every turn. It’s location for local exploring is particularly good with so...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £730 *

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Pippins is a 2 bedroom, dog friendly character cottage near Beaminster, Somerset.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £528 * booking fees included

Pippins

5360

2 bedroom, dog friendly character cottage near Beaminster, Somerset.


Pippins is a picture postcard country cottage nestled in the charming Somerset village of North Perrott - not far from the Dorset border. This cosy home can cater for all of the fa...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £528 *

Seymour Barn is a 2 bedroom, dog friendly barn conversion in Bridport, Dorset.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £862 * booking fees included

Seymour Barn

5314

2 bedroom, dog friendly barn conversion in Bridport, Dorset.


With the bustling market town of Bridport within striking distance, this beautiful barn conversion is the perfect home-away-from-home. A delightful spot to explore all the beauty a...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £862 *

Woodville Cottage is a 3 bedroom, dog friendly home near the beach in Lyme Regis.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Wed

7 nights from £737 booking fees included

Woodville Cottage

5151

3 bedroom, dog friendly home near the beach in Lyme Regis.


Woodville Cottage is a pretty and charming property, an annexe to a Grade II Listed Georgian building. Hidden away from the hustle and bustle of the elegant seaside town of Lyme Re...

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

7 nights from £737

Acorns is a 3 bedroom cottage in Corfe Castle, Dorset.
  • Sleeps 6 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £1186 booking fees included

Acorns

4828

3 bedroom cottage in Corfe Castle, Dorset.


Set on a private, secluded plot, Acorns is a wonderful family holiday home. Recently renovated to a very high standard, this detached house in the historic village of Corfe Castle ...

  • Sleeps 6 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £1186

Bay Tree Cottage is a 3 bedroom, dog friendly cottage near Bridport, Dorset.
  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £619 * booking fees included

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. Bay Tree Cottage offers all the deligh...

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

7 nights from £619 *

Rectory Cottage is a 2 bedroom cottage near Bridport, Dorset
  • Sleeps 4 + cot
  • No pets
  • Changeover Mon

7 nights from £724 booking fees included

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. As you pull into the spacious parking-area you will get ...

  • Sleeps 4 + cot
  • No pets
  • Changeover Mon

7 nights from £724

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Country walks under rust-coloured canopies following forest trails of red, yellow and orange. Reviving strolls along the coast and empty beaches, waves on the shore sending a shower of salty kisses across your cheeks. Gentle afternoons spent in quiet towns, freed from merry crowds and content in the last of summer's glow. Dorset in October half term is a perfect retreat away from the ebb and flow of everyday life. Find a cottage amongst our portfolio and take your little ones by the hand. A holiday is just around the corner and memories ready to be made.