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 129 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

129 Isle of Wight cottages for May Day bank holiday

New bookings can be placed for any holiday arriving on or after the 4th July 2020. COVID-19

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £303

1 bedroom self catering apartment with sea views in Seaview, Isle of Wight


This gorgeous top floor, one bedroom apartment has spectacular sea views over the rooftops across the Solent, and is just a few minutes from Seaview village and the beach. The Sai...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £303

View
  • 10% off

    17 Jul 2020 - 24 Jul 2020

    £525.00 £472.50

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £330

1 bedroom self catering apartment near the beach in Shanklin, Isle of Wight.


This contemporary studio apartment enjoys a great location in Shanklin. With modern decor and open plan living, it makes a cosy retreat for a couple looking for a coastal break. ...

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £330

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

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £330

1 bedroom self catering apartment near the beach in Shanklin, Isle of Wight.


Located on the first floor of Shanklin Villa, a lovely Victorian property, this small studio apartment packs a punch despite its size. Enjoying beautiful sea views from its elevate...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £330

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £369

1 bedroom self-catering cottage near Ventnor, Isle of Wight


Located in a rural village setting, Berryl Mead View is a delightful home from home cottage with plenty of space. It is well-equipped throughout and has an extremely comfortable li...

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £369

  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £425

1 bedroom, dog friendly holiday cottage near the sea near Ventnor, Isle of Wight


This gorgeous barn conversion is set within the grounds of the stunning North Grounds Farm, just outside the village of Chale Green on the southern side of the Island. For the envi...

  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £425

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £505

1 bedroom self catering apartment near the beach in Shanklin, Isle of Wight.


Sitting within a beautifully converted Victorian villa, The Cadogan Apartment offers a high standard of accommodation for a couple or lone traveller looking for a coastal break. Gu...

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £505

  • Sleeps 3 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £372

2 bedroom self catering cottage near the beach in Seaview.


Located in a small waterside development in a quiet corner away from the road on the edge of Seaview, 62 Buddleia Cottage is a pretty beach bungalow offering comfortable accommodat...

  • Sleeps 3 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £372

View
  • 20% off

    4 Jul 2020 - 11 Jul 2020

    £572.48 £457.98

  • Sleeps 3 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £435

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


This beautifully refurbished house is perfectly situated in the heart of Seaview Village, with a lovely decked area to the rear and outdoor seating so you can enjoy dining in the I...

  • Sleeps 3 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £435

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  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £366

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


Faithfull Cottage is a lovingly restored, pretty mid-terrace cottage which enjoys a rear garden and countryside views on the outskirts of St Helens. This comfortable cottage is set...

  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £366

View
  • 20% off

    4 Jul 2020 - 11 Jul 2020

    £566.07 £452.85

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £370

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


The Lobster Pot is a comfortably furnished beach bungalow located in a small waterside development on the edge of Seaview and next to a nature reserve. This beach bolt hole has dec...

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £370

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