May Day Bank Holiday on the Isle of Wight

With May Day bank holiday approaching, why not treat yourself to an idyllic retreat on the Isle of Wight? At Classic Cottages we have a range of holiday cottages offering wide variety and consistent quality. Take a look through our collection and let your imagination run away with ideas and plans for a luxury getaway; the Isle of Wight is beckoning. Read more

All around the Isle of Wight, May brings a splash of colour and lots of activity. With spring in its final throes and summer on its way, you can expect a pick up in pace and plenty to look forward. However you envisage your perfect getaway, be it a seaside sanctuary with ocean views, dog-friendly country cottage or spacious retreat big enough for all the family and friends, our collection of 119 Isle of Wight cottages available for May Day bank holiday will capture heart and mind. Pour through our portfolio and let your excitement build, a dream holiday is just around the corner. At Classic Cottages, we pride ourselves on marketing only the highest quality self-catering accommodation on the Isle of Wight. With each property handpicked and personally inspected, you can enjoy the best of the best this May. Secure your cottage today.  

Isle of Wight Ferry Booking With 200 ferries daily, our hassle free booking service makes your trip to the island plain sailing

119 Isle of Wight cottages for May Day bank holiday

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £550

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
  • Regret no pets
  • Changeover Sat

7 nights from £550

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £590

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


Bright and spacious, 10 Springfield Court is a second floor apartment set within eight acres of beautiful communal grounds. It would ideally suit a couple or small family. With...

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £590

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £590

2 bedroom self catering apartment near the beach in Seaview.


Apt 1 Springfield Court is a luxurious, ground floor apartment, set in an exclusive development in the picturesque village of Seaview. It would suit a small family or a couple in n...

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £590

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £596

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


Steeped in history Barton Manor is of great significance to the Isle of Wight’s heritage, situated adjacent to Osborne House and part of the original estate. The grand driveway lea...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £596

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

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £412

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


A Victorian property set on a quiet road and yards from the beach. Oaks is a well-equipped property, decorated to a high standard and perfect for families with open plan seating an...

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £412

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £425

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


1 The Saltings is a three-bedroom, lower ground floor apartment boasting a lovely beachfront location. It would ideally suit a family with children keen to enjoy the delights of th...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £425

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £445

2 bedroom self catering cottage at Island Harbour, near Newport.


Spring Tide is a delightful holiday cottage situated in a small development at Island Harbour Marina on the banks of the River Medina. The marina is set in a beautiful secluded val...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £445

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £453

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


4A Ship House, an attractive townhouse positioned right in the middle of Seaview, is perfect for a family looking for a coastal break. 'Ship shape' in presentation, the fantastic t...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £453

  • Sleeps 5 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £464

2 bedroom, dog friendly holiday apartment near the beach in Shanklin.


Park Lodge Annexe is a beautifully presented lower ground floor apartment within walking distance to the Rylstone Gardens and the Chine. The cliff path is a minute stroll away, lea...

  • Sleeps 5 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £464

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £498

3 bedroom self catering apartment with sea views in Seaview, Isle of wight.


Elm Cottage is a stylish first floor apartment brimming with character and comfort. It would suit friends traveling together, a couple or a family. From the front courtyard to t...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £498

Our property managers are local experts who handpick perfect places to stay.

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