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. 

10 self-catering cottages for October half term in Dorset

  • 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
  • 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

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

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

7 nights from £590

Toby's Hut

4723

1 bedroom, dog friendly shepherds hut near Lyme Regis, Dorset.


Located in the west Dorset Area of Outstanding Natural Beauty and just a 15 minute drive from fabulous Lyme Regis, Toby's Hut is a bespoke Shepherd's Hut, sitting in a perfect spot...

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

7 nights from £590

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

7 nights from £745

La Cabine Francaise

4726

1 bedroom, dog friendly Shpeherds Hut near Dorchester, Dorset.


Welcome to La Cabine Francaise, a glorious expanse of glamping bliss with a French twist. Set in the stunning Dorset countryside, this exclusive spot for two provides the perfect r...

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

7 nights from £745

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

7 nights from £486

September Cottage

2948

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

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £488

Ivy Cottage

4122

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 £488

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

7 nights from £558

Woodcutter's Cottage

4524

2 bedroom self catering cottage near Dorchester, Dorset.


Rolling hills, bustling market towns, rich history and stunning beaches - have we persuaded you to holiday in Dorset yet? Finding a lovely cottage to stay in is the only thing you ...

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

7 nights from £558

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

7 nights from £558

Poacher's Cottage

4522

2 bedroom self catering cottage near Dorchester, Dorset.


Tucked away in the picturesque village of Buckland Newton, Poacher's Cottage is one of four gorgeous properties making up Dominey's Yard. Situated perfectly for exploring the beaut...

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

7 nights from £558

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  • Sleeps 6 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £748

Meadows Barn

4293

3 bedroom self catering cottage near Yeovil, Dorset.


Meadows Barn is on the edge of the tranquil Dorset village of Halstock, with far reaching views over the surrounding countryside, ideal for a family holiday or a great base for fri...

  • Sleeps 6 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £748

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £813

Gardener's Cottage

4525

3 bedroom self catering cottage near Dorchester, Dorset.


A stay at Gardener's Cottage brings you everything you could wish for in a holiday location - spacious rooms, beautiful furnishings and a stunning setting complete with outdoor hea...

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £813