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 hereRead 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. 

Our exclusive ferry discounts will make your island trip with Classic plain sailing.

We have 1125 luxury self-catering cottages for the October half term

Coach House is a 3 bedroom, dog friendly self catering cottage near Lutterworth.
  • Sleeps 5 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1241

Coach House

5555

3 bedroom, dog friendly self catering cottage near Lutterworth.


A truly welcoming holiday home awaits your stay, located in the pleasant village of Cotesbach in rural Leicestershire right in the heart of the Midlands. This three bedroom luxury ...

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

7 nights from £1241

Lachlan's Barn is a 3 bedroom, dog friendly self catering cottage near Lutterworth.
  • Sleeps 6 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1314

Lachlan's Barn

5554

3 bedroom, dog friendly self catering cottage near Lutterworth.


Lachlan's Barn is a charming blend of rustic charm and modern comfort set within a beautifully converted farm building boasting open plan living and three en suite bedrooms. The...

  • Sleeps 6 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1314

Clifftops is a 3 bedroom self catering cottage with sea views in Hunstanton.
  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £1025

Clifftops

5758

3 bedroom self catering cottage with sea views in Hunstanton.


Clifftops is perfectly placed in a sought-after location in Hunstanton enjoying fabulous views of the lighthouse and changing tides, with front row seats to experience the amazing ...

  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £1025

To The Beach is a 3 bedroom, dog friendly holiday cottage near the beach near Pembroke.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £532 *

To The Beach

5776

3 bedroom, dog friendly holiday cottage near the beach near Pembroke.


To The Beach nestles just a short walk from the golden sands and rolling surf of West Angle Beach, in the historic seafaring village of Angle, offering a perfect blend of natural b...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £532 *

The Barton is a 1 bedroom, dog friendly cottage near the sea near Truro, Cornwall.
  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £621

The Barton

5752

1 bedroom, dog friendly cottage near the sea near Truro, Cornwall.


A stylish, boutique cottage which is the perfect romantic getaway, close to the tranquil shores of Restronguet Creek. This little hideaway is ideal for just the two of you, and of ...

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

7 nights from £621

Condurro House is a 3 bedroom, dog friendly cottage with sea views near Truro, Cornwall.
  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1002 *

Condurro House

5767

3 bedroom, dog friendly cottage with sea views near Truro, Cornwall.


With tranquil views of the mesmerising flow of the ebbing tide, this really is a relaxing retreat. Set in the heart of the peaceful village of St Clement on the Tresillian river, y...

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

7 nights from £1002 *

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

Pucks Oak is a 4 bedroom, dog friendly holiday cottage with sea views in Seaview.
  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £1050

Pucks Oak

5698

4 bedroom, dog friendly holiday cottage with sea views in Seaview.


Within moments of the seafront at Seaview, with off-street parking and a lovely garden, semi-detached Pucks Oak is a great home-from-home to enjoy with friends and family. With the...

  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £1050

The Lookout is a 2 bedroom, dog friendly apartment with sea views, near Studland.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £676

The Lookout

5763

2 bedroom, dog friendly apartment with sea views, near Studland.


In an elevated position with views out to Swanage Bay, The Lookout is a modern, stylish, first floor apartment for up to four lucky guests and their four-legged friend to enjoy. Ta...

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

7 nights from £676

Laundry Cottage is a 1 bedroom, dog friendly holiday cottage near Newquay, North Cornwall.
  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £703

Laundry Cottage

5709

1 bedroom, dog friendly holiday cottage near Newquay, North Cornwall.


Take the leafy drive that leads into the stunning Tresillian Estate where this little beauty is waiting to treat you and your loved one to a romantic getaway and wonderful escape f...

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

7 nights from £703

Tresillian House is a 8 bedroom, dog friendly holiday home near Newquay, North Cornwall.
  • Sleeps 16 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £4411

Tresillian House

5715

8 bedroom, dog friendly holiday home near Newquay, North Cornwall.


Looking for the fabulous getaway for a large family holiday, a celebratory escape or simply an excuse to get together with friends, then come and lord it up at the magnificent Tres...

  • Sleeps 16 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £4411

Loading more