Dorset Retreats for October Half Term

35 self-catering cottages for October half term in Dorset

2 Penny’s Cottages is a 3 bedroom house in the historic village of Corfe Castle, Dorset.
  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £866 booking fees included

2 Penny’s Cottages

2531

3 bedroom house in the historic village of Corfe Castle, Dorset.


Set in the historic village of Corfe Castle, 2 Penny's Cottages is a semi-detached family house that welcomes all its visitors, it is a real home-from-home. The property has been b...

  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £866

The Old School Gables is a 2 bedroom cottage near the market town of Bridport, Dorset.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £483 booking fees included

The Old School Gables

2490

2 bedroom cottage near the market town of 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 extrem...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £483

Hatts Barn is a 2 bedroom, rural holiday cottage near Shaftesbury, Dorset.
  • Sleeps 5 + cot
  • No pets
  • Changeover Fri

7 nights from £760 booking fees included

Hatts Barn

2093

2 bedroom, rural holiday cottage near Shaftesbury, Dorset.


Hatts Farm is a working farm located in a National Landscape. The farm spreads over 150 acres, located in the stunning countryside of the Dorset and Wiltshire border. Hatts Barn...

  • Sleeps 5 + cot
  • No pets
  • Changeover Fri

7 nights from £760

Barbridge Cottage is a 2 bedroom self catering cottage near Bridport, Dorset.
  • Sleeps 4 + cot
  • No pets
  • Changeover Sat

7 nights from £963 booking fees included

Barbridge Cottage

1805

2 bedroom self catering cottage near Bridport, Dorset.


Heading up the short, unmade track you will find the idyllic setting for the cottage. You enter into a wonderful, vaulted living space, flooded with the light and a cosy wood-burne...

  • Sleeps 4 + cot
  • No pets
  • Changeover Sat

7 nights from £963

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The Old Coach House is a 2 bedroom, dog friendly cottage near the county town of Dorchester, Dorset.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £574 * booking fees included

The Old Coach House

1386

2 bedroom, dog friendly cottage near the county town of Dorchester, Dorset.


This pretty detached former coach house can be found nestled in the grounds of the owner's property, in the rural Dorset countryside, within easy reach of the stunning coastlines o...

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

7 nights from £574 *