Holiday cottages for October in Dorset

Booking a Dorset holiday cottage in October sounds more like a winter break, but the summer can be extended by a few extra weeks down here. 

We’re not promising, but you could be on the beach enjoying the best the South and West has to offer. And at this time of year you can also bring the dog, or grab your surfboard as the Atlantic swells start rolling in and the sea is still warm, well fairly! If stormy seas don’t float your boat, it is a great time to explore the many gardens and woodlands in the area as they put on golden autumnal coats for their end of year display. Bring the family during October half-term to relive memories of a spent summer or indulge in a luxury short break before the winter kicks in. We have 47 holiday cottages for October in Dorset for you to choose from.

We've got 47 holiday cottages matching your search in Dorset...

6 bedroom thatched, dog friendly home near Lyme Regis, South Devon.


Buddlewall is an historic east Devon farmhouse, in a beautiful hidden rural setting, a short drive inland from the spectacular World Heritage east Devon and Dorset Jurassic Coast. ...

  • Sleeps 12 + 2 cots
  • Dogs welcome
  • Changeover Fri

Price per week £1482 - £1895


Lottie’s Loft is a luxurious first floor barn conversion, a gorgeous bolthole surrounded by beautiful Dorset countryside. Exterior steps lead from the decking to a balcony with bes...

  • Sleeps 6 in 2 properties
  • Changeover Fri

Price per week £832 - £1080


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 8 + 3 cots in 2 properties
  • Changeover Fri

Price per week £881 - £1157


Semi-detached Hatts Barn is a contemporary, reversed level barn conversion on a wide south-facing terrace. The large en suite master bedroom and a twin bedded family room (the beds...

  • Sleeps 9 + 2 cots in 2 properties
  • Changeover Fri

Price per week £915 - £1275

Our property managers are local experts who handpick perfect places to stay.


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 9 + 3 cots in 3 properties
  • Changeover Sat

Price per week £1131 - £1421


Glamping at Black Pig Retreats allows you to escape the everyday, park your car, load up your wheelbarrow and your countryside adventure begins; canvas living with a little of the ...

  • Sleeps 12 + 2 cots in 2 properties
  • Changeover Fri

Price per week £1173 - £1619


With a fabulous open plan interior, Furrow Lodge snuggles into the hillside in the delightful Dorset countryside and offers a real opportunity to escape from it all and slow the pa...

  • Sleeps 13 + 3 cots in 3 properties
  • Changeover Fri

Price per week £1494 - £1912