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. And don't forget, once you've paid your deposit, you can pay the remaining balance off in monthly instalments - find out more hereRead more

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

We have 1345 luxury self-catering cottages for the October half term

Hollyhocks is a 3 bedroom, dog friendly cottage near the beach in Kingsand, Cornwall.
  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £1029

Hollyhocks

6152

3 bedroom, dog friendly cottage near the beach in Kingsand, Cornwall.


Wind your way along the quiet country lanes to this charming rural retreat, tucked away in Cornwall's breathtakingly beautiful "forgotten corner". Boasting wonderful views of the s...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £1029

Wringford Cottages

  • Sleeps 30 + 8 cots in 5 properties
  • Changeover Sat

7 nights from £5688

Coniston is a
  • Sleeps 4
  • No pets

Coniston

213


Nestled on sought-after Scarlett Road in Castletown, this beautifully presented bungalow enjoys stunning sea views and offers a peaceful coastal retreat ideal for those seeking com...

  • Sleeps 4
  • No pets
Calf View is a Tranquil Cregneash cottage overlooking the Calf of Man
  • Sleeps 5 + cot
  • Dogs welcome

Calf View

206

Tranquil Cregneash cottage overlooking the Calf of Man


Perched above the timeless village of Cregneash, Calf View is a serene cottage with views framed by sweeping Manx vistas stretching towards shimmering seas and the wild beauty of t...

  • Sleeps 5 + cot
  • Dogs welcome
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Bramley Lodge is a 1 bedroom self catering cottage near Heathfield.
  • Sleeps 2 + cot
  • No pets
  • Changeover Fri

From £84 per night

Bramley Lodge

6137

1 bedroom self catering cottage near Heathfield.


Soak up the scenic views of this enchanting lodge that sits within an orchard in the High Weald National Landscape. Its peaceful location is the perfect escape for a romantic getaw...

  • Sleeps 2 + cot
  • No pets
  • Changeover Fri

From £84 per night

Fenella Cottage is a Stylish coastal cottage in Peel, moments from the sandy beach
  • Sleeps 5 + 2 cots
  • No pets

Fenella Cottage

212

Stylish coastal cottage in Peel, moments from the sandy beach


This beautifully finished coastal cottage in the heart of Peel offers an effortless blend of contemporary comfort and genuine homely charm, just moments from the town's historic ha...

  • Sleeps 5 + 2 cots
  • No pets
The Beach House is a 3 bedroom, dog friendly cottage with sea views near St Davids.
  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £590 *

The Beach House

6164

3 bedroom, dog friendly cottage with sea views near St Davids.


With a winning combination of contemporary comforts, character-filled living spaces, exposed beams and many other original features, just yards from the rolling surf at Abereiddy b...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £590 *

Bay Cottage is a 2 bedroom self catering cottage near the beach in Cowes.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £547

Bay Cottage

6150

2 bedroom self catering cottage near the beach in Cowes.


Tucked away in the charming village of Gurnard on the northwest coast of the Isle of Wight, this cosy two bedroom cottage offers a relaxed coastal lifestyle, complete with a pretty...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £547

Cuckoo Cottage is a 2 bedroom, dog friendly cottage near the beach in St Agnes, Cornwall.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £675

Cuckoo Cottage

6141

2 bedroom, dog friendly cottage near the beach in St Agnes, Cornwall.


This bijou bolthole has luxurious interiors and is set in a fabulous location in the heart of St Agnes. Cuckoo Cottage is a charming, terraced cottage which has been thoughtfully c...

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

7 nights from £675

Rheidiol Cottage is a 3 bedroom, dog friendly holiday cottage near the beach in St Davids.
  • Sleeps 5 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1400

Rheidiol Cottage

6149

3 bedroom, dog friendly holiday cottage near the beach in St Davids.


Let your next coastal adventure begin in splendid Rheidiol Cottage. Set in the heart of enchanting St Davids, on Wales' breathtaking Pembrokeshire coast, soak up the mystical vibe,...

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

7 nights from £1400

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

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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.