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 53 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.  

53 Isle of Wight cottages for May Day bank holiday

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

7 nights from £525

Willow Cottage

4517

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


This charming two bedroom cottage is located in the exclusive development of Island Harbour, with a gated entrance and private resident's parking. Willow Cottage has a sitting/dini...

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

7 nights from £525

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

7 nights from £536

Solent View Cottage

4389

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


This charming two bedroom cottage is situated in the pretty coastal village of Gurnard just outside Cowes, home to some spectacular Solent views and a prime location to watch the m...

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

7 nights from £536

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

7 nights from £625

The Dairy

4536

2 bedroom, dog friendly cottage near the beach near Brighstone, Isle of Wight.


The Dairy is the largest of all four barns and is closest to The Cattle Byre. It has a spacious kitchen and dining area making it a social space for the family to gather and make p...

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

7 nights from £625

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

7 nights from £625

Myrtle Dene

4508

2 bedroom self catering cottage with sea views in Wootton, Isle of Wight.


With views across the creek from both the garden and the first floor balcony, Myrtle Dene is a charming holiday home. Situated midway between Ryde and Newport, Wootton Creek is a g...

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

7 nights from £625

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

  • Sleeps 4
  • Regret no pets
  • Changeover Fri

7 nights from £800

The Retreat

3741

2 bedroom, rural self catering cottage with sea views in St Helens, Isle of Wight.


Set in an idyllic location by the water’s edge on St Helens Duver, The Retreat offers stunning accommodation for a family holiday on the Island. The property offers beautiful l...

  • Sleeps 4
  • Regret no pets
  • Changeover Fri

7 nights from £800

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £525

Spring Tide

3660

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 £525

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £775

Limpets

4622

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


This gorgeous home, just a stone's throw from the seafront, has sea views from the sitting-room and the luxury of your very own private garden, giving it all the ingredients for a ...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £775

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £900

2 Sea Whispers

3978

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


This charming first floor apartment is laid over two floors and situated right in the heart of Seaview village, tucked away down a quiet side street called Rope Walk, so-called as ...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £900

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

7 nights from £566

East Gull Sands

3595

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


East Gull Sands is an attached, comfortably furnished, beachfront holiday home in Seaview. Sitting right opposite the beach this property has sea views from the upstairs double bed...

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

7 nights from £566

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

7 nights from £600

30 Seaview Bay

3549

3 bedroom holiday cottage near the beach in Seaview, Isle of Wight.


30 Seaview Bay is a lovely three bedroom apartment set over two levels, offering sea views from the balcony of the master bedroom. Doors from the sitting-room lead to a decked-...

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

7 nights from £600

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

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