May Day Bank Holiday on the Isle of Wight

106 Isle of Wight cottages for May Day bank holiday

Hove To is a 2 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight
  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £424

Hove To

3767

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


The Isle of Wight is a fabulous place for a year-round holiday and Hove To is in a great location in the sought after village of Seaview on the eastern side of the Island. With vie...

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

7 nights from £424

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 £428

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 £428

Readymade beds and fluffy towels; this simple but appreciated welcome is standard with us.

1 St Josephs is a 2 bedroom self catering apartment with sea views in Ventnor, Isle of Wight
  • Sleeps 4 + cot
  • No pets
  • Changeover Sat

7 nights from £452

1 St Josephs

4183

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


With one of the best views on the Isle of Wight, 1 St Josephs is a superb ground floor apartment beautifully decorated throughout. The property has a large patio-area spanning two ...

  • Sleeps 4 + cot
  • No pets
  • Changeover Sat

7 nights from £452

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  • 50% off

    30 May 2026 - 6 Jun 2026

    £904.00 £452.00

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

7 nights from £460

Faithfull Cottage

3600

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


Faithfull Cottage is a welcoming retreat situated within two miles distance of St Helens village on the Isle of Wight, as well as a gorgeous beach, RSPB Nature Reserve and the vill...

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

7 nights from £460

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

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 £510

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 £510

6 St Josephs is a 2 bedroom self catering apartment with sea views in Ventnor, Isle of Wight
  • Sleeps 4 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £522

6 St Josephs

3846

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


6 St Josephs is a top floor apartment with stunning panoramic sea views, which you can admire from the balcony, sitting-room and main bedroom! Ideally positioned between Bonchurch ...

  • Sleeps 4 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £522

Quiet Corner Cottage is a 2 bedroom, dog friendly holiday cottage near the beach in Bembridge, Isle of Wight.
  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £539

Quiet Corner Cottage

3646

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


Bembridge is a much sought-after pretty village on the east of the Isle of Wight and Quiet Corner Cottage is a cosy semi-detached bungalow, perfectly situated just a mile from the ...

  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £539

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

10 Bayclose is a 2 bedroom self catering apartment with sea views in Freshwater, Isle of Wight
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £547

10 Bayclose

5159

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


Overlooking the gorgeous coastline at Freshwater Bay sits 10 Bayclose, a wonderfully homely apartment perfect for a family getaway to the seaside. With light and airy interiors, sn...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £547

Bay Cottage is a 2 bedroom self catering cottage near the beach in Cowes.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £547

Bay Cottage

6150

2 bedroom self catering cottage near the beach in Cowes.


Tucked away in the charming village of Gurnard on the northwest coast of the Isle of Wight, this cosy two bedroom cottage offers a relaxed coastal lifestyle, complete with a pretty...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £547

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