Cottages for May bank holidays in Isle of Wight

May is when Isle of Wight comes alive, the winter is left behind and a sunny day feels like summer in a early May bank holiday cottage.

A sunny day in May can feel like summer, especially in Isle of Wight. The schools have gone back. And the May calendar in the South West is bursting with high days, holidays and Pagan customs so peculiar you couldn't make them up. Have a peek at what's available. Use the search options on the left to choose the length of your break and the area where you want to stay. We've got 56 holiday cottages available in Isle of Wight for your May escape.

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We have 56 available for the May Day bank holiday in Isle of Wight

4 bedroom self catering cottage near the beach in Ryde, Isle of Wight.


Rosa Monte is a semi-detached property with three double bedrooms and a children's bunk bedroom, accommodating eight in total. Situated just off Ryde esplanade it’s a short walk in...

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Sat

Price per week £995

4 bedroom converted barn with far reaching rural views in St Helens, Isle of Wight.


Hill Farm Barn is an immaculately presented and impressively converted 18th Century Threshing Barn standing in half acre of private grounds. Perched on a hilltop half a mile from a...

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Sat

Price per week £1270

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


A spectacular waterfront three-storey house situated on Seaview duver with uninterrupted sea views from the kitchen/dining-room and the first floor balcony. Just a few steps from y...

  • Sleeps 8 + 2 cots
  • Regret no pets
  • Changeover Sat

Price per week £1350

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


This pretty attached Victorian cottage sits in the grounds of the Priory Estate and comes with use of its many diversions. With 70 acres of grounds to explore, plus a stunning priv...

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

Price per week £1382

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


2 Little Cedars is a sleek and modern property, with a light and clean finish throughout. Split over three floors, and stylishly decorated with luxury furnishings, this delightful ...

  • Sleeps 9 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

Price per week £1138

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


The Old Boat House is an attractive period cottage set in a fantastic waterfront location on the edge of the beach at Seagrove Bay. This is a charming family home and can be rented...

  • Sleeps 9 + cot
  • Regret no pets
  • Changeover Fri

Price per week £1308

Dogs go free on holidays starting between 29th June to 5th July.

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


Orchard House is a wonderful property for an extended family looking for a sprawling holiday home near the beach in Bembridge. The downstairs living areas are inviting - no doubt t...

  • Sleeps 10 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

Price per week £1027

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  • 10% off

    30 Jun 2018 - 7 Jul 2018

    £1186.73 £1068.30

  • 10% off

    7 Jul 2018 - 14 Jul 2018

    £1574.37 £1416.60

6 bedroom, dog friendly self catering home near the beach in Ryde, Isle of Wight.


Full of character, Pelham Lodge is a top destination for a large group of friends or an extended family looking for a house for a celebratory occasion. Just a short stroll from Ryd...

  • Sleeps 14 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £2078


If you are looking for a traditional cottage, look no further than Blakes Barn. Constructed from Island stone, the charm starts outside Blakes Barn with the beautiful brick work, t...

  • Sleeps 8 + 2 cots in 2 properties
  • Changeover Fri

Price per week £917