Book your Christmas & New Year stay this summer and you'll receive a luxury hamper worth £120.

October Breaks in Dorset

Pick from 46 cottages in Dorset this October

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 £865 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 £865

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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

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  • 40% off

    17 Jul 2026 - 24 Jul 2026

    From £735.00 £466.20 booking fees included

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

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

7 nights from £922 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 £922

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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 £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 *

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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

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

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