Cottages for October Half Term

Cottages for October Half Term

Gently releasing its grip on summer, October often enjoys warm weather and soft sunshine. Embrace the t-shirt weather a little longer and enjoy a self-catering retreat this October half term. From quaint one-bed cottages to spacious retreats big enough for all the family, we can help you piece together the perfect autumn holiday in a luxury cottage. Take a look at our collection and secure your favourite one today. Plus, you can now pay your holiday in monthly instalments! Find out more here.  Read more

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

We have 1162 luxury self-catering cottages for the October half term

Prestons Barn is a 2 bedroom, dog friendly holiday cottage near Crediton, North Devon.
  • Sleeps 4 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £494

Prestons Barn

5869

2 bedroom, dog friendly holiday cottage near Crediton, North Devon.


This beautifully presented retreat is perfect for exploring the unspoilt countryside which surrounds it. From the beautiful woodland trails and hikes which lead from your doorstep ...

  • Sleeps 4 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £494

Isla Rose is a Dog friendly shepherds hut near Pulborough.
  • Sleeps 2
  • Dogs welcome (1 only)
  • Changeover Fri

From £89 per night

Isla Rose

5948

Dog friendly shepherds hut near Pulborough.


This oh-so-romantic shepherd's hut for two lies in the beautiful countryside of West Sussex and offers an idyllic, peaceful escape that's dog friendly too. Just a mere two hours...

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

From £89 per night

Little Oak Farm

  • Sleeps 8 in 4 properties
  • Changeover Fri

7 nights from £397

Sunset Skies is a 2 bedroom self catering apartment with sea views in Hunstanton.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £675

Sunset Skies

5865

2 bedroom self catering apartment with sea views in Hunstanton.


Welcome to Sunset Skies - a stylish, first floor apartment located in the seaside town of Hunstanton, aptly named due to the way the sky lights up at dusk, bursting into bold, vibr...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £675

Low Rigg is a 3 bedroom, dog friendly self catering cottage near Hawes.
  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £667

Low Rigg

5770

3 bedroom, dog friendly self catering cottage near Hawes.


Come and enjoy a break in the Yorkshire Dales and relax with the rustic charm of an original Yorkshire stone cottage. Semi-detached Low Rigg is huddled at the edge the charming vil...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £667

Millook is a 2 bedroom lodge with sea views near Bude, North Cornwall.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £742

Millook

5937

2 bedroom lodge with sea views near Bude, North Cornwall.


Escape to north Cornwall and delight in a view that will captivate your imagination, giving you the freedom to breathe and relax into your holiday! This striking lodge not only boa...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £742

Trebarwith is a 3 bedroom, dog friendly lodge with sea views near Bude, Cornwall.
  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £994

Trebarwith

5879

3 bedroom, dog friendly lodge with sea views near Bude, Cornwall.


With breathtaking views across Bude and the gorgeous north Cornwall coastline, thanks to the floor to ceiling windows, this unique and beautifully crafted, dog-friendly luxury lodg...

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £994

7 Chapel Street is a 2 bedroom, dog friendly cottage near the beach in Mousehole.
  • Sleeps 3 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £484 *

7 Chapel Street

5872

2 bedroom, dog friendly cottage near the beach in Mousehole.


Tucked away in the heart of the historic fishing village of Mousehole, 7 Chapel Street is a sweet two bedroom cottage offering a perfect coastal escape. Brimming with charm, the co...

  • Sleeps 3 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £484 *

Be in the know… Sign up to our newsletter for holiday inspiration, offers and all things Classic.

2 Old Turnpike Cottages is a 2 bedroom, dog friendly self catering cottage with hot tub near Chipping Norton.
  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £888

2 Old Turnpike Cottages

5866

2 bedroom, dog friendly self catering cottage with hot tub near Chipping Norton.


Tucked away in the picturesque village of Middle Barton, just a short drive from Chipping Norton and the exclusive Soho Farmhouse lies this quintessential, dog-friendly Cotswold Co...

  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £888

27 Marine Parade is a 3 bedroom holiday cottage with sea views in St Mawes, South Cornwall.
  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £855

27 Marine Parade

5856

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


Perfectly positioned in St Mawes overlooking the clear blue sea towards St Anthony Head and beyond, 27 Marine Parade is a stone’s throw away from the pretty harbour and gorgeous be...

  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £855

Load more

October can be the most colourful month of the year, with trees parading their final flourish before stripping bare for the winter. Take the kids on a half term holiday to remember and soak up the last hints of green. A day out to a public garden might not be first on the children's list of things to do but running through tunnels lined with golden leaves and feeling the crunch underfoot will soon have them jumping in leafy mounds with excitement. The sea has a magical quality, reflecting the October sky and sparkling on the horizon. It doesn't matter if the weather takes a turn for the wintery worse, as a good storm will liven up any school holiday - stand safely back from the sea and feel the salty spray. Once you've finished exploring, return to your very own private retreat and relax in total comfort.