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. 

28 self-catering cottages for October half term in Dorset

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

7 nights from £395

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 Owner’s home, The Stables is self-cont...

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

7 nights from £395

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  • 20% off

    21 Dec 2018 - 28 Dec 2018

    £578.65 £463.20

  • 20% off

    28 Dec 2018 - 4 Jan 2019

    £578.65 £463.20

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

7 nights from £397

1 bedroom, rural cottage near the beach near Bridport, Dorset.


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

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

7 nights from £397

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  • 20% off

    29 Dec 2018 - 5 Jan 2019

    £522.00 £417.60

We’re a Visit England Quality Accredited Agency for our high standards in holiday letting.

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

7 nights from £397

1 bedroom, rural cottage near the beach near Bridport, Dorset.


The Dairy is another extremely comfortable single-storey cottage in this small and friendly farm development. This property has French windows to its own enclosed outside space – t...

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

7 nights from £397

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  • 20% off

    22 Dec 2018 - 29 Dec 2018

    £522.00 £417.60

  • 20% off

    29 Dec 2018 - 5 Jan 2019

    £522.00 £417.60

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

7 nights from £400

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


This cosy, compact yet 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...

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

7 nights from £400

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £407

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 £407

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

7 nights from £436

1 bedroom thatched self catering cottage near Sherborne, Dorset.


Pound Farm Cottage is a hidden gem; this listed thatched cottage has been thoughtfully renovated to create a spacious, stylish holiday home, retaining many of the original features...

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

7 nights from £436

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  • 25% off

    17 Dec 2018 - 23 Dec 2018

    £635.00 £476.25

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £561

Beach Chalet on the beach sleeping two in Lyme Regis, Dorset.


Imagine a holiday right on the seashore of a very special beach, relaxing on your veranda with a glass of something refreshing, watching the gentle waves at one of the most famous ...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £561

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £409

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 £409

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

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £453

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 areas creates a very sociable space for a couple or sma...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £453

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  • 40% off

    21 Dec 2018 - 28 Dec 2018

    £651.55 £391.20

  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £453

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 £453

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