Luxury Cottages in May on the Isle of Wight

See our range of 77 available cottages in May on the Isle of Wight

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 £795 booking fees included

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 £795

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 £1067 booking fees included

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 £1067

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 £1859 booking fees included

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 £1859

View
  • 5% off

    24 Jul 2026 - 31 Jul 2026

    £3346.00 £3181.85 booking fees included

  • 20% off

    31 Aug 2026 - 4 Sep 2026

    From £1638.75 £1323.60 booking fees included

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 £1871 booking fees included

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 £1871

Lucaster is a 3 bedroom, dog friendly holiday cottage near the beach in Fishbourne, Isle of Wight
  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £887 booking fees included

Lucaster

4307

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


This gorgeous, cosy, former coastguard's cottage sits in a peaceful setting in Fishbourne and is just a few yards from the sea and the welcoming local pub. Lucaster is perfectly pl...

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

7 nights from £887

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 £1795 booking fees included

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 £1795

We’ve been raising the standards of self catering holidays since 1977.

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 £1465 booking fees included

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 £1465

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 £1182 booking fees included

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 £1182

Oak Tree Cottage is a 3 bedroom self catering cottage with sea views in Seaview, Isle of Wight
  • Sleeps 6 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £1308 booking fees included

Oak Tree Cottage

4212

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


With gorgeous views over the Solent and the beach just a few steps away, Oak Tree Cottage is a delightful reverse level holiday home situated a short stroll from the village centre...

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

7 nights from £1308

The New House is a 4 bedroom self catering cottage in Godshill, Isle of Wight
  • Sleeps 8 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1479 booking fees included

The New House

4025

4 bedroom self catering cottage in Godshill, Isle of Wight


Nestled in the heart of the chocolate-box village of Godshill, this detached house has beautiful secluded gardens to the rear and everything the village can offer within a few minu...

  • Sleeps 8 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1479

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