Cottages for October half term in South England

We have 144 luxury self catering cottages for the October half term in South England

Inglefield is a 4 bedroom, dog friendly holiday cottage near the beach in St Helens.
  • Sleeps 7 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £908 *

Inglefield

5637

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


This beautiful home close to Bembridge Harbour is a space to enjoy with family and friends. From exploring the bays and beaches to the rolling countryside and historic castles, Ing...

  • Sleeps 7 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £908 *

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  • 30% off

    29 Aug 2025 - 5 Sep 2025

    From £1138.00 £796.60

Beacon Hill Barn is a 2 bedroom self catering cottage near Midhurst.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £791

Beacon Hill Barn

5644

2 bedroom self catering cottage near Midhurst.


This gorgeous barn sits in the heart of the South Downs National Park providing an excellent base for all types of rural pursuits and is perfectly positioned for visiting the towns...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £791

Darjeeling Lodge is a 2 bedroom, dog friendly self catering cottage near Rye.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £581

Darjeeling Lodge

5598

2 bedroom, dog friendly self catering cottage near Rye.


If you're looking for a peaceful or romantic break in the heart of the Sussex countryside, then this is the place for you! Situated in Beckley, near the village of Broak Oak, Darje...

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

7 nights from £581

Escape Away is a 2 bedroom self catering cottage near the beach in Freshwater.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £732 *

Escape Away

5612

2 bedroom self catering cottage near the beach in Freshwater.


Close to the beach, a short drive from pretty Yarmouth and not far from the iconic Needles, Escape Away is the perfect luxury retreat to base yourself for a peaceful and relaxing h...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £732 *

Driftwood is a 2 bedroom, dog friendly holiday cottage near the beach in Freshwater, Isle of Wight.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £656 *

Driftwood

5613

2 bedroom, dog friendly holiday cottage near the beach in Freshwater, Isle of Wight.


Whisk yourself away to this pretty retreat on the glorious Isle of Wight, perfect for couples and families and your four-legged companions who love to explore as much as you do. Th...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £656 *

Colwell Bay Cottages

  • Sleeps 8 + 2 cots in 2 properties
  • Changeover Fri

7 nights from £1388

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

4 Church Square is a 1 bedroom, dog friendly self catering cottage in Rye.
  • Sleeps 2
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £622

4 Church Square

5520

1 bedroom, dog friendly self catering cottage in Rye.


Welcome to this gorgeous Grade II Listed cottage situated along one of Rye's famous cobbled streets, perfect for couples looking to stay in the heart of Rye. As you enter this ...

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

7 nights from £622

Halland Rise is a 4 bedroom, dog friendly holiday cottage with sea views in Seaview, Isle of Wight.
  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1463 *

Halland Rise

5500

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


Introducing Halland Rise, a stunning detached house sleeping eight guests, nestled in Seaview, one of the Island's most sought-after villages. With a choice of hidden coves and lon...

  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1463 *

View
  • 20% off

    16 Aug 2025 - 22 Aug 2025

    From £2647.80 £2118.24

Costers Lodge is a 3 bedroom, dog friendly self catering cottage in Midhurst.
  • Sleeps 6 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1400

Costers Lodge

5490

3 bedroom, dog friendly self catering cottage in Midhurst.


Sitting in gorgeous countryside, this 100 year old luxury sandstone cottage is just a stone's throw from Cowdray House and only a five-minute drive from the centre of Midhurst. It'...

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

7 nights from £1400

Tap Cottage is a 3 bedroom, dog friendly cottage in the heart of Stockbridge and close to Winchester
  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1655

Tap Cottage

5417

3 bedroom, dog friendly cottage in the heart of Stockbridge and close to Winchester


Within the bustling village of Stockbridge, this contemporary cottage has been renovated to an exceptional standard. There is so much to explore locally; with sites such as Salisbu...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1655

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