Dorset Retreats for October Half Term

44 self-catering cottages for October half term in Dorset

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

7 nights from £759 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 £759

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

7 nights from £963 booking fees included

Barbridge Cottage

1805

2 bedroom, rural holiday 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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  • 25% off

    25 Jul 2026 - 1 Aug 2026

    £1323.00 £1008.00 booking fees included

  • 25% off

    1 Aug 2026 - 8 Aug 2026

    £1323.00 £1008.00 booking fees included

  • 25% off

    8 Aug 2026 - 15 Aug 2026

    £1323.00 £1008.00 booking fees included

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 £573 * 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 in the rural Dorset countryside, within easy reach of the stunning coastlines of the Jurassic Coast, a World Heritage Site. ...

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

7 nights from £573 *

Sunnyholme is a 4 bedroom house near the beach in Studland, Dorset.
  • Sleeps 6 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £933 booking fees included

Sunnyholme

1460

4 bedroom house near the beach in Studland, Dorset.


The Isle of Purbeck is a stunning National Landscape between Poole and Swanage, boasting one of the most spectacular coastlines in Dorset. Sunnyholme is an extremely spacious de...

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

7 nights from £933