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 77 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

77 Isle of Wight cottages for May Day bank holiday

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

7 nights from £475

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


If you're looking for a property that's practically on the beach, then this is it! 1 Starboard House perches just opposite the beach in central Seaview and enjoys uninterrupted sea...

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

7 nights from £475

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

7 nights from £475

2 bedroom, rural self catering cottage near the beach in Brighstone, Isle of Wight


One of two beautifully converted barns right in the heart of the Island's Area of Outstanding Natural Beauty. Equipped and decorated to a high standard mixing the charming features...

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

7 nights from £475

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

7 nights from £475

2 bedroom self catering cottage with sea views in Seaview.


North View is a wonderful holiday hideaway just on the outskirts of Seaview with sea views across the Solent from the kitchen/dining-room and first floor bedrooms. Set back from th...

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

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

  • 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 + 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

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

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

7 nights from £553

2 bedroom, rural holiday apartment near the beach in Freshwater, Isle of Wight


This beautiful contemporary apartment is literally perched above the beach, offering stunning views of the picturesque Freshwater Bay. Extremely well appointed, the apartment offer...

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

7 nights from £553

View
  • 50% off

    26 Apr 2019 - 3 May 2019

    £733.65 £367.00

  • 30% off

    3 May 2019 - 10 May 2019

    £790.51 £553.70

  • 20% off

    10 May 2019 - 17 May 2019

    £825.56 £660.80

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

7 nights from £785

2 bedroom, this holiday cottage is near the beach in St Helens, Isle of Wight.


Little Black Barn at Hill Farm is a beautifully converted property of a contemporary style, set in a stunning south facing location at the top of a hill on the outskirts of St.Hele...

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

7 nights from £785

  • 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

Loading more