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. 

27 self-catering cottages for October half term in Dorset

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

7 nights from £357

The Stables

1965

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 £357

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

7 nights from £363

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
  • Regret no pets
  • Changeover Sat

7 nights from £363

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

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

7 nights from £363

The Dairy

2663

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 doors to its own enclosed outside space – the...

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

7 nights from £363

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

7 nights from £367

Owl's Nest Cottage

2942

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 £367

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £377

Badgers Cottage

3014

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 £377

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £414

Pound Farm Cottage

4076

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
  • Regret no pets
  • Changeover Fri

7 nights from £414

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £505

The Chalet on the Beach

3351

Cabin 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 £505

  • Sleeps 3 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £415

Wayside Cottage

4484

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


A gorgeous, chocolate-box cottage that is the ideal escape, nestled in the heart of one of Dorset's picturesque villages. Just a stone's throw from the lovely local pub, Wayside Co...

  • Sleeps 3 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £415

We’re here to help you find your perfect place to stay 7 days a week.

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £390

The Old School Gables

2490

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 £390

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

7 nights from £412

Old Sandpitts Cottage

4504

2 bedroom thatched self catering cottage near Bridport, Dorset.


Tucked away down its own private track, this picture-perfect thatched cottage is a little gem. Surrounded by its own private garden, the cottage is very peaceful and offers space f...

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

7 nights from £412

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