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

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. 

19 self-catering cottages for October half term in Dorset

  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £343

1 bedroom, rural 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
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £343

  • Sleeps 2
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £346

1 bedroom, dog friendly self catering cottage near Sherborne, Dorset.


This cosy, compact, delightful bolthole for two is set in a wonderfully tranquil hamlet in north Dorset with village shops and a choice of two pubs within two miles. Built in lo...

  • Sleeps 2
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £346

Need more time? Reserve any cottage for up to 24 hours before booking.

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £352

1 bedroom, dog friendly self catering cottage near Bridport, Dorset.


Badgers Cottage, a snug semi-detached cottage for two, is set in a farmyard, beautifully converted from an 18th Century stone barn. All on one level, the open plan design gives a w...

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £352

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £363

1 bedroom, rural holiday cottage near Dorchester, Dorset.


Dorset’s World Heritage Jurassic Coast is close to this comfortably furnished, single-storey, spacious cottage. Set within the grounds of the Owners' home, (who may not be resident...

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £363

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £514 *

3 bedroom thatched, dog friendly cottage in Tolpuddle, Dorset.


This pretty thatched cottage is in the tranquil historic village of Tolpuddle, just 15 miles from the World Heritage Jurassic Coast. An ideal base for a family holiday or perfect f...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £514 *

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £375

2 bedroom dog friendly holiday cottage near 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 extreme...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £375

  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £413

2 bedroom thatched, dog friendly cottage near Dorchester, Dorset.


Beehive Cottage is a charming and cosy cottage for four, on a quiet lane opposite St Mary's church in the village of Puddletown. The village is surrounded by farmland, Thomas Hardy...

  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £413

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  • 15% off

    20 Dec 2019 - 27 Dec 2019

    £659.85 £561.00

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £413

2 bedroom, dog friendly holiday cottage near Dorchester, Dorset.


Cedar Lodge is a cosy cottage in a quiet rural location. All on one level, the open plan living-room with kitchen and dining-area creates a very sociable space for a couple or smal...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £413

We’ve been raising the standards of self catering holidays since 1977.

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £421

2 bedroom, rural holiday cottage near Shaftesbury, Dorset.


Dairyman’s Cottage is traditional yet contemporary, semi-detached and set on a south-facing terrace. The property has a welcoming feel, with a stunning open plan design downstairs,...

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £421

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £430

2 bedroom holiday cottage near Bridport, Dorset.


Close to Dorset's spectacular Jurassic Coast, the popular market town of Bridport and the harbour and beach at West Bay, this cottage has stunning views of the gentle Dorset countr...

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £430

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  • 10% off

    6 Dec 2019 - 13 Dec 2019

    £430.04 £387.00

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