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 100 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

100 Isle of Wight cottages for May Day bank holiday

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £750

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


Bay Cottage is a lovely three bedroom detached property on the outskirts of Seaview village, located in Seagrove Manor Road, a quiet spot yet just a few minutes walk into the villa...

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £750

  • Sleeps 6 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £775

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


Located on the corner of Ryde Road, Westbourne is a lovely property ideally placed for Seaview Village and the beach. The village amenities are just a few minute's stroll away and ...

  • Sleeps 6 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £775

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £795

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


This lovely, light and spacious detached house located on Fairy Road in Seaview, just a short stroll from the seafront, makes a fantastic base for a wonderful holiday on the Isle o...

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £795

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £795

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


Right in the heart of Seaview village, this semi-detached property has been completely renovated, with a Skandi theme, to offer a wonderful place to stay on the Isle of Wight. With...

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £795

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

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £816

3 bedroom, dog friendly cottage near the beach in Bembridge.


Ledge View is a beautifully renovated semi-detached home just steps away from Forelands beach, lined with quirky beach huts, stretches of white sand, rock pools and an acclaimed ca...

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £816

View
  • 50% off

    2 Mar 2019 - 9 Mar 2019

    £660.74 £330.50

  • 50% off

    9 Mar 2019 - 16 Mar 2019

    £660.74 £330.50

  • 50% off

    16 Mar 2019 - 23 Mar 2019

    £660.74 £330.50

  • Sleeps 6 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £900

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


With a stunning spacious sea facing balcony, Oak Tree Cottage is in a superb location just steps from the beach and a short walk along the seafront into Seaview Village. An outdoor...

  • Sleeps 6 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £900

  • Sleeps 6
  • Regret no pets
  • Changeover Fri

7 nights from £1195

3 bedroom self catering houseboat with sea views in Bembridge, Isle of Wight


Welcome aboard this luxury two-storey houseboat in Bembridge harbour with two rear balconies and a private pontoon, you can kayak right up to your back door just in time for lunch....

  • Sleeps 6
  • Regret no pets
  • Changeover Fri

7 nights from £1195

  • Sleeps 7 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £559

3 bedroom, dog friendly holiday cottage near the beach in Totland, Isle of Wight


If you long for picturesque walks in the daytime and quiet nights under starry skies, then Ashmead Cottage is your holiday ideal. This lovely property would suit a family or even t...

  • Sleeps 7 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £559

  • Sleeps 7 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £676

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


This light, beautifully presented holiday home offers quality accommodation with wooden floors, whitewashed walls and interesting prints and furnishings lending splashes of colour ...

  • Sleeps 7 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £676

  • Sleeps 7 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £850

3 bedroom self catering apartment with sea views in Seagrove Bay, Isle of Wight


In the most spectacular location just a few metres from Seagrove Bay, this two-storey apartment is in a prime holiday location with a large decked balcony to admire the stunning se...

  • Sleeps 7 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £850

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

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