October Breaks in Dorset

Great weather often hangs around until well into October in Dorset, so to celebrate the final flourishes of summer properly why not book a luxury self-catering cottage? Snugly one-bed retreat in a charming town, romantic hideaway with amazing sea views, or cottage in the country with space for all the gang, we'll help you pave the way to the holiday of your dreams this October. Read more

For a truly romantic getaway, browse through our list of cottages with hot tubs available this October. Spend your days exploring and soaking in the last of the summer rays, and then when you've had your fill return to your home-from-home and hop into a bubbling hot tub. Or how about a family-friendly cottage, perfect for little kids and big kids alike? October is a great time of year for families to make the most of all that Dorset has to offer with half term around the corner and lots of spook-tacular celebrations taking place ahead of Halloween. If you would like to revel in some peace and quiet, we have plenty of secluded cottages, offering lots of privacy and plenty of space for some quality R&R. At Classic Cottages, we pride ourselves on marketing the finest self-catering cottages around, handpicking and personally inspecting each one. Find your favourite today. 

Pick from 38 cottages in Dorset this October

  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1010

4 bedroom, dog friendly cottage with sea views in Lyme Regis, Dorset.


Escape to the coast and this fabulous cottage where you can watch the seascape change all day long. Just minutes from the harbour at Lyme Regis and its iconic Cobb, this Grade I...

  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1010

  • Sleeps 9 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £845

5 bedroom, dog friendly self catering cottage near Bridport, Dorset.


This beautiful stone farmhouse has something very special indeed – it comes with a 450 acre wildlife and nature reserve and a unique relationship with Dorset Wildlife Trust. Quite ...

  • Sleeps 9 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £845

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

  • Sleeps 10 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1516

5 bedroom, dog friendly cottage near the beach near Lyme Regis.


Less than half a mile from the World Heritage Jurassic Coast, The Old Manor House is a beautiful 16th Century, Grade II Listed house, full of character with a delightful enclosed g...

  • Sleeps 10 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1516

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  • 10% off

    30 Apr 2019 - 3 May 2019

    £1051.40 £946.26

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

7 nights from £1625

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

7 nights from £1625

  • Sleeps 6 in 2 properties
  • Changeover Fri

7 nights from £959


These two delightful properties, set deep in Dorset's beautiful countryside, are the ultimate rural retreats! To set the scene, a long, unmade farm track leads to West Farm, where ...

  • Sleeps 6 in 2 properties
  • Changeover Fri

7 nights from £959

  • Sleeps 8 + 2 cots in 2 properties
  • Changeover Fri

7 nights from £1055


West Hembury Farm is situated in an Area of Outstanding Natural Beauty; a walker's paradise. Just four miles from the bustling market town of Bridport, and a short drive to the Wo...

  • Sleeps 8 + 2 cots in 2 properties
  • Changeover Fri

7 nights from £1055

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

7 nights from £1020


Hatts Farm is a working farm set in 100 acres on the Dorset/Wiltshire border, in an Area of Outstanding Natural Beauty near the market town of Shaftesbury and within driving distan...

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

7 nights from £1020

  • Sleeps 9 + 3 cots in 3 properties
  • Changeover Sat

7 nights from £1296


This working farm on the edge of the historic village of Chideock stretches gently downhill to the Jurassic Coast where one of Dorset's most famous landmarks – Golden Cap – rises a...

  • Sleeps 9 + 3 cots in 3 properties
  • Changeover Sat

7 nights from £1296

Readymade beds and fluffy towels; this simple but appreciated welcome is standard with us.