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 52 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.  

52 Isle of Wight cottages for May Day bank holiday

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

7 nights from £639

The Pigsty

4538

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


The Pigsty is a detached barn with parking for two cars and two private seating areas alongwith a spacious communal area. There are two bedrooms, a double and a twin, each beau...

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

7 nights from £639

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

7 nights from £639

The Stables

4537

2 bedroom, dog friendly self catering cottage near Brighstone, Isle of Wight.


The Stables is light and airy throughout with two bedrooms, a king-size double and a twin. The open plan living-room with kitchen and dining areas is warm and inviting, with doors ...

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

7 nights from £639

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

7 nights from £806

The Clock House

4559

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


This beautifully decorated converted former stable, in the grounds of the Old Rectory in Yaverland just outside Bembridge, is a real gem. The owner has created a stylish and indivi...

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

7 nights from £806

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

7 nights from £832

Pinings Yard

4625

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


This gorgeous, tucked away cottage is just a short stroll from the centre of Yarmouth and a real delight. Gated access off a narrow unmade track, leading to the sea, takes you to y...

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

7 nights from £832

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

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

7 nights from £895

Starboard Side

4736

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


This gorgeous and beautifully presented cottage is within walking distance of lovely Gurnard beach and has wonderful sea views from the first floor main bedroom. The owner of Starb...

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

7 nights from £895

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

7 nights from £994

Daisy Cottage

4824

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


Daisy Cottage is a lovely cosy and welcoming mid terrace cottage nestled in the heart of Bembridge. Located in one of the most desirable areas to live in on the Isle of Wight, this...

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

7 nights from £994

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

7 nights from £1138

Sea Lights

4967

2 bedroom self catering apartment with sea views in Cowes, Isle of Wight.


Situated close to the beating heart of world-famous Cowes, lies the pretty coastal village of Gurnard. This handsome coastal ground floor apartment, comfortably sleeps four within ...

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

7 nights from £1138

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

7 nights from £767

Elm Cottage

3597

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


Elm Cottage is a stylish first floor apartment brimming with character and comfort. It would suit friends travelling together, a couple or a family. From the front courtyard to ...

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

7 nights from £767

  • Sleeps 5 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £813

Sunnyside

4960

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


Perfectly situated in the much sought-after village of Seaview on the Isle of Wight, Sunnyside is an appealing dog friendly holiday abode fully refurbished in 2021/22. It is set i...

  • Sleeps 5 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £813

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

7 nights from £613

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 £613

Choose from our exclusive collection at the best prices with real time availability.

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