Luxury Cottages in May on the Isle of Wight

See our range of 72 available cottages in May on the Isle of Wight

The Dairy is a 2 bedroom, dog friendly cottage near the beach near Brighstone, Isle of Wight.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £737

The Dairy

4536

2 bedroom, dog friendly cottage near the beach near Brighstone, Isle of Wight.


The dairy is a warm and welcoming barn conversion perfect for slow mornings, costal adventures and cosy evenings by the fire. Being is the largest of the four barns at Kingston, an...

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

7 nights from £737

The Stables  is a 2 bedroom, dog friendly self catering cottage near Brighstone, Isle of Wight.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £650

The Stables

4537

2 bedroom, dog friendly self catering cottage near Brighstone, Isle of Wight.


The heart of the property is an inviting open plan living space where the sitting, dining and kitchen areas are thoughtfully brought together. Soft natural light filters in through...

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

7 nights from £650

The Pigsty is a 2 bedroom, dog friendly cottage near the beach near Brighstone, Isle of Wight.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £650

The Pigsty

4538

2 bedroom, dog friendly cottage near the beach near Brighstone, Isle of Wight.


Tucked away in a picturesque and peaceful spot just outside the village of Shorwell, this charming barn conversion makes a wonderful base for a relaxed getaway. The Pigsty at Kings...

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

7 nights from £650

Kingston Barns

  • Sleeps 15 + 4 cots in 4 properties
  • Changeover Sat

7 nights from £2670

Solas is a 4 bedroom self catering cottage with sea views in Seaview, Isle of Wight.
  • Sleeps 8 + cot
  • No pets
  • Changeover Sat

7 nights from £1378

Solas

4459

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


This superb, spacious detached house close to Seaview village has wonderful sea views from the first floor open plan sitting/dining-room and balcony. Taking full advantage of the v...

  • Sleeps 8 + cot
  • No pets
  • Changeover Sat

7 nights from £1378

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 £794

Pebbles

4398

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


Seaview is a wonderful place for an Isle of Wight holiday and Pebbles is perfectly situated in the heart of the village on a quiet residential street just a stone's throw away from...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £794

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 £762

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 £762

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 £1059

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 £1059

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 £997

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 £997

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 £1765

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 £1765

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