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. 

18 self-catering cottages for October half term in Dorset

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

7 nights from £350

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 £350

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

7 nights from £354

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 £354

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

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

7 nights from £356

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 £356

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

7 nights from £356

1 bedroom, dog friendly 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 £356

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

7 nights from £415

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

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £426

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 create a very sociable space for a couple or smal...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £426

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £436

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


This pretty, detached former coach house is in beautiful rural Dorset, and within easy reach of the stunning World Heritage Jurassic coastline. The Old Coach House has a spaciou...

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £436

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

7 nights from £462

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 £462

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

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £478

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


Imagine life in a tranquil Dorset village and Ivy Cottage is just the sort of place you may picture in your mind. Set in the midst of an Area of Outstanding Natural Beauty, the cot...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £478

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

7 nights from £486

2 bedroom self catering cottage near the sea near Weymouth, Dorset.


This comfortable semi-detached family home is on the edge of the countryside, yet only three miles from Weymouth with its sandy beaches and historic quay. A 20 minute walk takes yo...

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

7 nights from £486

Loading more