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 94 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

94 Isle of Wight cottages for May Day bank holiday

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £475

2 bedroom, dog friendly self catering cottage in a rural setting close to Godshill, Isle of Wight


Bagwich Barn Cottage is located in a stunning setting within the grounds of the main house and with two other barns available for larger parties. A charming sun-room to the front o...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £475

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £489

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


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 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £489

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

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

7 nights from £500

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


This is a wonderfully secluded property with a charming garden and spacious balcony, all within a few minutes from the idyllic Seagrove Bay in Seaview. There are several steps up t...

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

7 nights from £500

  • Sleeps 4 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £525

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


6 St Joseph’s has stunning panoramic sea views, which you can sit and admire from the balcony, living room and master bedroom! Ideally positioned between Bonchurch and Ventnor this...

  • Sleeps 4 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £525

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

7 nights from £535

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


Venice Lodge is a Georgian cottage located in a quiet residential area of the popular seaside town of Ryde. This is a unique house that you will not soon forget. If you long for th...

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

7 nights from £535

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  • 20% off

    22 Feb 2019 - 1 Mar 2019

    £425.93 £340.74

  • 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 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

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  • 20% off

    22 Feb 2019 - 1 Mar 2019

    £340.73 £272.59

  • 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

View
  • 20% off

    22 Feb 2019 - 1 Mar 2019

    £343.69 £274.95

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

  • 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

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  • 20% off

    22 Feb 2019 - 1 Mar 2019

    £358.59 £286.87

  • 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

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  • 20% off

    29 Mar 2019 - 5 Apr 2019

    £405.31 £324.00

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