Isle of Wight Cottages for May Half-Term

We have 51 May half-term cottages on the Isle of Wight

Berry Cabin is a 2 bedroom, dog friendly, bolthole in Seaview, Isle of Wight.
  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £662 booking fees included

Berry Cabin

5286

2 bedroom, dog friendly, bolthole in Seaview, Isle of Wight.


What a little cutie! Berry Cabin is a delightful bolthole for four guests and one well behaved doggy looking for some summer fun! Surrounded by Hersey nature reserve and countrysid...

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

7 nights from £662

Underwood Cabin is a 3 bedroom, dog friendly self catering cottage near Yarmouth, Isle of Wight.
  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £1252 booking fees included

Underwood Cabin

4995

3 bedroom, dog friendly self catering cottage near Yarmouth, Isle of Wight.


Nestled next to St Hubert's Lodge surrounded by tranquil woodlands and green pastures, Underwood Cabin is a delightful rural retreat, perfectly situated on the edge of the Isle of ...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £1252

Valdora is a 3 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £1077 booking fees included

Valdora

4959

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


Perfectly situated in the heart of the charming village of Seaview, Valdora is a gorgeous holiday retreat, beautifully styled to offer the very best in contemporary living. Seaview...

  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £1077

Oystercatcher is a 3 bedroom luxury houseboat in Bembridge, Isle of Wight.
  • Sleeps 6
  • No pets
  • Changeover Fri

7 nights from £1498 * booking fees included

Oystercatcher

4869

3 bedroom luxury houseboat in Bembridge, Isle of Wight.


Set in picturesque Bembridge Harbour with far reaching views out to the Solent, Oystercatcher is a luxurious houseboat, beautifully furnished and just waiting to welcome you on boa...

  • Sleeps 6
  • No pets
  • Changeover Fri

7 nights from £1498 *

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

7 nights from £817 booking fees included

Westhill View

4882

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


With the golden sands of Shanklin beach a short walk away, this lovely holiday home sits in the heart of town, perfect for traditional days by the seaside and within easy reach of ...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £817

9 The Ruskins  is a 3 bedroom self catering cottage near the beach in Bembridge, Isle of Wight.
  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £1599 booking fees included

9 The Ruskins

4865

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


This delightful family holiday home can be found just a short stroll from the beautiful beaches of Bembridge and a wonderful array of traditional shops and restaurants. Light fille...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £1599

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

Daisy Cottage  is a 2 bedroom, dog friendly holiday cottage near the beach in Bembridge, Isle of Wight.
  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £1204 booking fees included

Daisy Cottage

4824

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


Daisy Cottage is a lovely cosy and welcoming mid terrace cottage nestled in the heart of Bembridge. Located in one of the most desirable areas to live in on the Isle of Wight, this...

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

7 nights from £1204

Old Bembridge House is a 3 bedroom, dog friendly holiday cottage near the beach in Bembridge, Isle of Wight.
  • Sleeps 6
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £1180 booking fees included

Old Bembridge House

4791

3 bedroom, dog friendly holiday cottage near the beach in Bembridge, Isle of Wight.


Perfectly located just moments away from the beach and pretty harbour, Old Bembridge House has all the makings of the perfect holiday idyll on the Isle of Wight. Laid across three-...

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

7 nights from £1180

Starboard Side is a 2 bedroom, dog friendly holiday cottage near the beach in Cowes, Isle of Wight.
  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1043 booking fees included

Starboard Side

4736

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


This gorgeous and beautifully presented cottage is within walking distance of lovely Gurnard beach and has wonderful sea views from the first floor main bedroom. The owner of Starb...

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

7 nights from £1043

1 Harrow Cottages is a 1 bedroom self catering apartment near the beach in Seaview, Isle of Wight.
  • Sleeps 2 + cot
  • No pets
  • Changeover Sat

7 nights from £481 booking fees included

1 Harrow Cottages

4642

1 bedroom self catering apartment near the beach in Seaview, Isle of Wight.


This charming first floor apartment is in Nettlestone, just up the hill from Seaview and within walking distance of the beach. Surrounded by countryside there are lovely views from...

  • Sleeps 2 + cot
  • No pets
  • Changeover Sat

7 nights from £481

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