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 1350 available cottages. Read more

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

We've got 1350 holiday cottages available for October

Ruska is a Luxury cabin for two with an outdoor bath, privately nestled in the Forest of Dean.
  • Sleeps 2
  • No pets
  • Changeover Fri

From £230 per night + £53 booking fees

Ruska

6209

Luxury cabin for two with an outdoor bath, privately nestled in the Forest of Dean.


Sitting in the Gloucestershire countryside, this lakeside retreat for two offers a peaceful and romantic getaway. This gorgeous cabin has been lovingly handcrafted with luxury in m...

  • Sleeps 2
  • No pets
  • Changeover Fri

From £230 per night

Quarterbridge House is a Impressive Douglas home with private gardens and tennis court
  • Sleeps 6 + 2 cots
  • Dogs welcome

Quarterbridge House

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

Reserve your 2027 holiday for just £40.00

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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
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Rubena Cottage is a 2 bedroom, dog friendly cottage near the beach in Port Isaac.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £588 booking fees included

Rubena Cottage

6200

2 bedroom, dog friendly cottage near the beach in Port Isaac.


A mere hop, skip and a jump from the water's edge, this absolute gem of a cottage has been restored with exquisite care, creating a most desirable retreat that's perfect for warm s...

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

7 nights from £588

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

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

7 nights from £861 booking fees included

St Peter's House

6202

2 bedroom self catering cottage in Gloucester.


Set within Gloucester Cathedral's grounds with a magnificent glimpse of the Cathedral spires from the impressive staircase, St Peter's House enjoys a truly amazing location. A hous...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £861

Round Table House is a A unique countryside retreat with breathtaking southern views
  • Sleeps 8 + cot
  • Dogs welcome

Round Table House

218

A unique countryside retreat with breathtaking southern views


Round Table House stands high above the rolling countryside of Ronague, a remarkable retreat where contemporary style meets the character of a much-loved home. Its elevated positio...

  • Sleeps 8 + cot
  • Dogs welcome
Bottle Lodge is a Grade II Listed, lovingly restored 1807 Bottle Lodge for two in Staffordshire.
  • Sleeps 2
  • No pets
  • Changeover Fri

From £100 per night + £53 booking fees

Bottle Lodge

6206

Grade II Listed, lovingly restored 1807 Bottle Lodge for two in Staffordshire.


Sitting in the Staffordshire countryside at the entrance to Tixall Estate, a unique and historic stay awaits at Bottle Lodge - named for its quirky octagonal shape that looks like ...

  • Sleeps 2
  • No pets
  • Changeover Fri

From £100 per night

Hawcombe Cottage is a 1 bedroom, dog friendly cottage with sea views near Tavistock.
  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £624 booking fees included

Hawcombe Cottage

6205

1 bedroom, dog friendly cottage with sea views near Tavistock.


Tucked away in the pretty riverside village of Bere Ferrers, Hawcombe Cottage is a charming hideaway for two, perfectly placed for those seeking a peaceful escape surrounded by the...

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

7 nights from £624

Arrive at your handpicked holiday home safe in the knowledge it’s been fully inspected.

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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 1350 holiday cottages for October for you to choose from.