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 1237 available cottages. Read more

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

We've got 1237 holiday cottages available for October

Harmon Vale is a 5 bedroom, dog friendly holiday cottage with sea views in Solva.
  • Sleeps 10 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £1020 *

Harmon Vale

6015

5 bedroom, dog friendly holiday cottage with sea views in Solva.


Seaside serenity, spacious comfort, breathtaking sea views, and a blissful spa tub, that’s Harmon Vale. This stunning holiday home is the perfect destination for families, friends ...

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

7 nights from £1020 *

St Harmon  is a 5 bedroom, dog friendly holiday cottage with sea views in Solva.
  • Sleeps 10 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1020 *

St Harmon

6016

5 bedroom, dog friendly holiday cottage with sea views in Solva.


Enjoy a blissful coastal break in St Harmon, a superb three-storey property with luxurious hot tub, located in one of the prettiest harbour villages in Wales, in Upper Solva, nestl...

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

7 nights from £1020 *

Blackberry Cottage is a 4 bedroom, dog friendly holiday cottage near the beach in Heacham.
  • Sleeps 8 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1147 *

Blackberry Cottage

5983

4 bedroom, dog friendly holiday cottage near the beach in Heacham.


Nestled within a row of quaint cottages and close to the sandy dunes and beaches of South Beach, this gorgeous dog-friendly retreat can be enjoyed year-round with loved ones as wel...

  • Sleeps 8 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1147 *

View
  • 20% off

    29 Aug 2025 - 5 Sep 2025

    From £1360.00 £1088.00

14 Regent Terrace is a 2 bedroom, dog friendly, lower ground floor apartment with sea views in Penzance.
  • Sleeps 4 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £485 *

14 Regent Terrace

6004

2 bedroom, dog friendly, lower ground floor apartment with sea views in Penzance.


Tucked away just behind the iconic promenade in Penzance and mere moments from the Jubilee Pool and the sparkling sea beyond, 14 Regent Terrace is a restored two bedroom traditiona...

  • Sleeps 4 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £485 *

The Granary is a 2 bedroom self catering cottage near Moretonhampstead, South Devon.
  • Sleeps 4 + cot
  • No pets
  • Changeover Thu

7 nights from £972

The Granary

6010

2 bedroom self catering cottage near Moretonhampstead, South Devon.


If it's a superb rural retreat you are looking for, look no further, The Granary at Greenawell Farm is the perfect package. The Granary is a beautiful stone cottage, finished to an...

  • Sleeps 4 + cot
  • No pets
  • Changeover Thu

7 nights from £972

Greenawell Farm Cottages

  • Sleeps 9 + 4 cots in 3 properties
  • Changeover Fri

7 nights from £1998

The Little Woodland House is a Family size cabin with hot tub near Fowey, South Cornwall.
  • Sleeps 5 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £669 *

The Little Woodland House

6001

Family size cabin with hot tub near Fowey, South Cornwall.


Welcome to The Little Woodland House, a peaceful yet full-of-life glamping retreat nestled in the picturesque Fowey Valley. This thoughtfully crafted wooden cabin is ideal for a ro...

  • Sleeps 5 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £669 *

Carter's Cottage is a 1 bedroom self catering cottage near Hailsham.
  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £479

Carter's Cottage

6005

1 bedroom self catering cottage near Hailsham.


This cosy and well-appointed semi-detached country retreat sits on a working heavy horse farm, perfect for couples or solo travellers looking to unwind, reconnect and enjoy the slo...

  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £479

View
  • 10% off

    29 Aug 2025 - 5 Sep 2025

    £617.00 £555.30

We are Gold accredited with the Green Tourism Business Scheme.

Port and Starboard
 is a 4 bedroom holiday cottage with sea views in St Mawes, South Cornwall.
  • Sleeps 8 + cot
  • No pets
  • Changeover Sat

7 nights from £1113

Port and Starboard

5982

4 bedroom holiday cottage with sea views in St Mawes, South Cornwall.


In prime position overlooking St Mawes Bay with wonderful seascape views, beautiful interiors and gorgeous contemporary furnishings, semi-detached Port and Starboard is a fabulous ...

  • Sleeps 8 + cot
  • No pets
  • Changeover Sat

7 nights from £1113

Hobbit Corner is a 1 bedroom, dog friendly holiday cottage near Looe, South Cornwall.
  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £413

Hobbit Corner

5959

1 bedroom, dog friendly holiday cottage near Looe, South Cornwall.


Wind your way along the leafy lanes to the peaceful hamlet of Trevelmond, in the heart of southeast Cornwall, where this little beauty is waiting to welcome you with open arms and ...

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

7 nights from £413

Load more

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 1237 holiday cottages for October for you to choose from.