May half term holiday cottages

We've got 26 holiday cottages matching your search in the South of England...

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 £797

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 £797

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 £1827

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 £1827

Need more time? Reserve any cottage for up to 24 hours before booking.

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 £1455

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 £1455

Grace Cottage is a 1 bedroom holiday cottage close to the sea near Ventnor, Isle of Wight
  • Sleeps 2 + cot
  • No pets
  • Changeover Fri

7 nights from £622

Grace Cottage

4209

1 bedroom holiday cottage close to the sea near Ventnor, Isle of Wight


This gorgeous barn conversion is set within the grounds of the stunning North Grounds Farm, just outside the village of Chale Green on the southern side of the Island. For the envi...

  • Sleeps 2 + cot
  • No pets
  • Changeover Fri

7 nights from £622

2 Bermuda is a 2 bedroom self catering apartment with sea views in Seaview, Isle of Wight.
  • Sleeps 4 + cot
  • No pets
  • Changeover Sat

7 nights from £501

2 Bermuda

3517

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


Welcome to 2 Bermuda, a rather lovely first floor apartment nestled in the charming village of Seaview, with wonderful views stretching across the Solent - ideal for an unforgettab...

  • Sleeps 4 + cot
  • No pets
  • Changeover Sat

7 nights from £501

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

7 nights from £850

Spinnakers

3659

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


Situated in a peaceful, private estate just a short stroll from the charming seaside town of Yarmouth, Spinnakers is a cosy, single-storey semi-detached holiday home with well-kept...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £850