Dorset Retreats for October Half Term

44 self-catering cottages for October half term in Dorset

Barn Owls Cottage is a 3 bedroom, dog friendly cottage near Bridport, Dorset.
  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £667 * booking fees included

Barn Owls Cottage

3015

3 bedroom, dog friendly cottage near Bridport, Dorset.


Barn Owls Cottage is a semi-detached cottage that has been converted from an 18th Century stone barn. Despite having stylish modern fittings, it has still retained much of its orig...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £667 *

West Hembury Farm

  • Sleeps 8 + 2 cots in 2 properties
  • Changeover Fri

7 nights from £1183.08 booking fees included

Beech Cottage is a 5 bedroom, dog friendly cottage with views over the nature reserve near Bridport, Dorset.
  • Sleeps 9 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1249 booking fees included

Beech Cottage

2887

5 bedroom, dog friendly cottage with views over the nature reserve near Bridport, Dorset.


This beautiful stone farmhouse has something very special indeed - it comes with a 450 acre nature reserve and a unique relationship with Dorset Wildlife Trust, offering comfortabl...

  • Sleeps 9 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1249

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  • 20% off

    17 Jul 2026 - 21 Jul 2026

    £1769.25 £1428.00 booking fees included

Sturthill Stable is a 3 bedroom, dog friendly barn conversion set within a working farm near Bridport, Dorset.
  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £737 booking fees included

Sturthill Stable

2829

3 bedroom, dog friendly barn conversion set within a working farm near Bridport, Dorset.


This beautiful barn conversion at the heart of a working farm is just inland from Dorset's spectacular Jurassic Coast and its beaches. The rural setting will please all the family ...

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

7 nights from £737

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

The Linhay is a 1 bedroom cottage near the beach near Bridport, Dorset.
  • Sleeps 2 + cot
  • No pets
  • Changeover Sat

7 nights from £384 booking fees included

The Linhay

2661

1 bedroom cottage near the beach near Bridport, Dorset.


The Linhay is a tucked away single-storey retreat – and an ideal base for exploring the wonderful coastline. The cottage nestles alongside the barns, with a fully enclosed gravel c...

  • Sleeps 2 + cot
  • No pets
  • Changeover Sat

7 nights from £384

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  • 20% off

    25 Jul 2026 - 1 Aug 2026

    £545.00 £448.60 booking fees included

The Parlour is a 2 bedroom cottage with views of Golden Cap near Bridport, Dorset
  • Sleeps 5 + cot
  • No pets
  • Changeover Sat

7 nights from £582 * booking fees included

The Parlour

2662

2 bedroom cottage with views of Golden Cap near Bridport, Dorset


The Parlour is an excellent choice for a family, with French doors opening out onto an enclosed gravelled patio, comfortable accommodation for five guests – one of the three single...

  • Sleeps 5 + cot
  • No pets
  • Changeover Sat

7 nights from £582 *

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  • 20% off

    8 Aug 2026 - 15 Aug 2026

    From £1191.80 £966.04 booking fees included

The Dairy is a 1 bedroom cottage close to the Jurassic Coast, near Bridport, Dorset.
  • Sleeps 2 + cot
  • No pets
  • Changeover Sat

7 nights from £384 booking fees included

The Dairy

2663

1 bedroom cottage close to the Jurassic Coast, near Bridport, Dorset.


The Dairy is an extremely comfortable single-storey cottage in this small and friendly farm development. The property has French doors to its own enclosed outside space – the patio...

  • Sleeps 2 + cot
  • No pets
  • Changeover Sat

7 nights from £384

Doghouse Farm

  • Sleeps 9 + 3 cots in 3 properties
  • Changeover Sat

7 nights from £1350.36 booking fees included

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

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

View
  • 40% off

    24 Jul 2026 - 31 Jul 2026

    £693.00 £441.00 booking fees included

  • 40% off

    31 Jul 2026 - 7 Aug 2026

    £693.00 £441.00 booking fees included

Each and every one of our cottages is fully equipped with everything you’ll need on holiday.

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