Holiday Cottages for October

Holiday Cottages for October

Booking a holiday cottage in October may sound like a winter break, but summer often extends its stay and graces October with glorious sunshine and warm weather. With quiet weeks and an opportunity to take the kids away for half term, there are lots of things to look forward to however you'd like to spend your holiday. Get started and browse our 1224 available cottages. Read more

Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.

We've got 1224 holiday cottages available for October

Eriska is a Luxury dog friendly cabin for two in the Scottish Highlands.
  • Sleeps 2
  • Dogs welcome (1 only)
  • Changeover Fri

From £266 per night + £18 booking fees

Eriska

6219

Luxury dog friendly cabin for two in the Scottish Highlands.


Tucked away in the hills within the magical landscapes of the Scottish Highlands, Eriska is just the place for a tranquil escape for two (and the dog!). This elegant Scandi-styl...

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

From £266 per night

Ailsa is a Luxury dog friendly cabin for two in the Scottish Highlands.
  • Sleeps 2
  • Dogs welcome (1 only)
  • Changeover Fri

From £266 per night + £18 booking fees

Ailsa

6222

Luxury dog friendly cabin for two in the Scottish Highlands.


With sweeping views across heather covered mountains, patch-work forests and crystal-clear lochs, Ailsa is a secluded, luxurious cabin for two, deep in the heart of the Scottish Hi...

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

From £266 per night

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Highbury House is a Luxury group getaway in the heart of historic Castletown
  • Sleeps 8 + 2 cots
  • No pets

Highbury House

220

Luxury group getaway in the heart of historic Castletown


Set in the heart of historic Castletown, Highbury House is a beautifully renovated four-bedroom property offering stylish and spacious accommodation across three floors. Finished t...

  • Sleeps 8 + 2 cots
  • No pets
Cobblers Cottage is a 2 bedroom, dog friendly cottage near the sea in Hartland, Devon.
  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £673 booking fees included

Cobblers Cottage

6218

2 bedroom, dog friendly cottage near the sea in Hartland, Devon.


Tucked away in the heart of Hartland village, just a short drive from the dramatic coastline, beautiful beaches and spectacular coastal paths of north Devon, Cobblers Cottage is a ...

  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £673

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Sea Whisper is a 5 bedroom holiday cottage near the beach in Croyde, North Devon.
  • Sleeps 8 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £2064 booking fees included

Sea Whisper

6173

5 bedroom holiday cottage near the beach in Croyde, North Devon.


Sea Whisper is a spacious, recently refurbished, five-bedroom family home in the heart of Croyde on the north Devon coast, sleeping up to eight guests. Set within a large private g...

  • Sleeps 8 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £2064

New Mill is a 2 bedroom, dog friendly holiday cottage near Bovey Tracey, Dartmoor.
  • Sleeps 5 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £660 booking fees included

New Mill

6191

2 bedroom, dog friendly holiday cottage near Bovey Tracey, Dartmoor.


Welcome to this rather unique holiday retreat. New Mill is a rather deceiving name for this Grade II Listed watermill, which boasts many stunning original features, lovingly preser...

  • Sleeps 5 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £660

Greystones at Ago's Leap is a Impressive Douglas home with private gardens and tennis court
  • Sleeps 6 + 2 cots
  • Dogs welcome

Greystones at Ago's Leap

221

Impressive Douglas home with private gardens and tennis court


Set along Quarterbridge Road in Douglas, Greystones is a striking and spacious home offering an impressive place to stay within easy reach of the Island's capital. Beautifully p...

  • Sleeps 6 + 2 cots
  • Dogs welcome
Goaf Cottage is a 2 bedroom, dog friendly self catering cottage near Whitby.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £796 booking fees included

Goaf Cottage

6204

2 bedroom, dog friendly self catering cottage near Whitby.


In a county of hills, dales and sandy beaches, you will find the moors village of Glaisdale and nestled in a sleepy lane sits Goaf Cottage, an old farm building converted into a go...

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

7 nights from £796

Ballacosney Cottage is a Stylish Laxey cottage with private gym and sauna
  • Sleeps 6 + cot
  • No pets

Ballacosney Cottage

219

Stylish Laxey cottage with private gym and sauna


Tucked away up a peaceful lane above Laxey, Ballacosney Cottage is a beautifully renovated retreat designed with relaxing island stays in mind. Fresh, modern and filled with natura...

  • Sleeps 6 + cot
  • No pets
Hooper's House is a 4 bedroom self catering cottage in Gloucester.
  • Sleeps 6 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £1085 booking fees included

Hooper's House

6203

4 bedroom self catering cottage in Gloucester.


Hooper's House is a centuries-old property sitting in harmony with the historic buildings of Gloucester Cathedral but with a contemporary interior vibe, mixing traditional and mode...

  • Sleeps 6 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £1085

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We’re not promising, but it's not uncommon to be able to sit on the beach in October enjoying bright sunshine, particularly hot in a sheltered corner. And at this time of year you can also bring the dog with you as the doggy beach ban is lifted in September. Bring your bag, ball and a bowl for water, and you could spend hours playing games and relaxing on the beach, occasionally dipping your toes in the sea to cool off. October is also a great time to explore gardens and woodlands 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 1224 holiday cottages for October for you to choose from.