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 118 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

118 Isle of Wight cottages for May Day bank holiday

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

7 nights from £291

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


West Flatlet is situated right in the heart of Seaview village and is perfect for couples looking for a coastal break. This small but cosy and comfortable first floor flat sits at ...

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

7 nights from £291

  • 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 just a few minutes from Seaview village and the beach. Newly deco...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £303

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

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £333

1 bedroom, rural self catering cottage in Newport, Isle of Wight


This absolutely gorgeous barn conversion is the perfect place for a couple's holiday, located on the Durton Farm Estate in the centre of the Island. Lovingly refurbished by the own...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £333

  • 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, well equipped throughout and extremely comfortable living room wit...

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

7 nights from £369

  • 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

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  • 20% off

    25 Oct 2019 - 1 Nov 2019

    £470.00 £376.00

  • 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 on the edge of Seaview, 62 Buddleia Cottage is a pretty beach bungalow offering comfortable accommodation, for a couple or small family, in...

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

7 nights from £372

  • 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

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

7 nights from £505

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


Offering a high standard of accommodation, The Worsley Apartment is a ground floor apartment within Shanklin Villa, a beautifully converted Victorian building. With a separate kitc...

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

7 nights from £505

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

  • 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

  • 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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