Holiday cottages for October in South England

Holiday cottages for October in South England

Savour the crunch of leaves underfoot, the quiet beaches and the autumnal woodland with a holiday cottage in the UK for October half term.Read more

We’re not promising, but you could be on the beach enjoying the best the South and West has to offer. And at this time of year you can also bring the dog, or grab your surfboard as the Atlantic swells start rolling in and the sea is still warm, well fairly! If stormy seas don’t float your boat, it is a great time to explore the many gardens and woodlands in the area 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.

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

We've got 147 holiday cottages matching your search in the South of England...

Pebbles is a 2 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £750

Pebbles

4398

2 bedroom self catering cottage near the beach in Seaview, Isle of Wight.


This beautifully refurbished house is perfectly situated in the heart of Seaview Village, with a lovely patio area to the rear and outdoor seating so you can enjoy dining in the Is...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £750

Winkle Cottage is a 2 bedroom self catering cottage near the beach in Cowes, Isle of Wight.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £785

Winkle Cottage

4395

2 bedroom self catering cottage near the beach in Cowes, Isle of Wight.


This gorgeous terraced cottage, situated in the Conservation Area of the old town of Cowes, is just a few minutes' walk from the centre of town, offering the perfect family holiday...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £785

We’re a Visit England Quality Accredited Agency for our high standards in holiday letting.

Longdown Hall is a 3 bedroom self catering cottage with sea views in Ventnor, Isle of Wight
  • Sleeps 6 + 2 cots
  • No pets
  • Changeover Sat

7 nights from £854

Longdown Hall

4386

3 bedroom self catering cottage with sea views in Ventnor, Isle of Wight


A stunning property in Ventnor on the southern tip of the Island, with the most sensational 180 degree sea views from the sun-drenched patio. Relax with your breakfast in the sunsh...

  • Sleeps 6 + 2 cots
  • No pets
  • Changeover Sat

7 nights from £854

Solent View Cottage is a 2 bedroom self catering cottage near the beach in Cowes, Isle of Wight.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £545

Solent View Cottage

4389

2 bedroom self catering cottage near the beach in Cowes, Isle of Wight.


This charming two bedroom cottage is situated in the pretty coastal village of Gurnard, just outside Cowes, home to some spectacular Solent views and a prime location to watch the ...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £545

Beggars Roost is a 3 bedroom self catering apartment with sea views in Seaview, Isle of Wight
  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £904

Beggars Roost

4346

3 bedroom self catering apartment with sea views in Seaview, Isle of Wight


This gorgeous first floor apartment in the heart of Seaview village is perfectly placed to reach everything within a few minutes' walk. The seafront is just around the corner, a po...

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

7 nights from £904

Dolphin Cottage is a 4 bedroom self catering cottage near the beach in Bembridge, Isle of Wight
  • Sleeps 8 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £1138 *

Dolphin Cottage

4347

4 bedroom self catering cottage near the beach in Bembridge, Isle of Wight


Within a few minutes’ walk of the village centre and located on an unmade road leading to the sea, Dolphin Cottage is a simply stunning house ideally laid out to make space for all...

  • Sleeps 8 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £1138 *

Fortune is a 4 bedroom, dog friendly holiday houseboat with sea views in Bembridge, Isle of Wight
  • Sleeps 8
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £1730

Fortune

4336

4 bedroom, dog friendly holiday houseboat with sea views in Bembridge, Isle of Wight


Step on board this simply stunning houseboat situated in the picturesque Bembridge harbour, just a short walk from Bembridge village. The beautiful bright yellow door opens to a va...

  • Sleeps 8
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £1730

Buckland House is a 4 bedroom self catering cottage near the beach in Seaview, Isle of Wight
  • Sleeps 8 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £1800

Buckland House

4290

4 bedroom self catering cottage near the beach in Seaview, Isle of Wight


Tucked out of sight yet right in the heart of Seaview, Buckland House is a stunning home, beautifully renovated by the owners and just a stone's throw from the beach and local vill...

  • Sleeps 8 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £1800

Readymade beds and fluffy towels; this simple but appreciated welcome is standard with us.

Merivale is a 4 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight
  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £1263

Merivale

4240

4 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight


This lovely, light and spacious detached house located on Fairy Road in Seaview, just a short stroll from the seafront, makes a fantastic base for a wonderful holiday on the Isle o...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £1263

House of Logs is a 4 bedroom, rural self catering cottage near the beach in Totland, Isle of Wight
  • Sleeps 8 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £888

House of Logs

4225

4 bedroom, rural self catering cottage near the beach in Totland, Isle of Wight


House of Logs is a unique and stunning property located on the west coast of the Island, just a short walk from Widdick Chine and Totland Bay. Perfect for a peaceful holiday and do...

  • Sleeps 8 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £888

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