May Day Bank Holiday on the Isle of Wight

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 115 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.  

Our exclusive ferry discounts will make your island trip with Classic plain sailing.

115 Isle of Wight cottages for May Day bank holiday

6 St Josephs is a 2 bedroom self catering apartment with sea views in Ventnor, Isle of Wight
  • Sleeps 4 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £522

6 St Josephs

3846

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


6 St Josephs is a top floor apartment with stunning panoramic sea views, which you can admire from the balcony, sitting-room and main bedroom! Ideally positioned between Bonchurch ...

  • Sleeps 4 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £522

Quiet Corner Cottage is a 2 bedroom, dog friendly holiday cottage near the beach in Bembridge, Isle of Wight.
  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £533

Quiet Corner Cottage

3646

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


Bembridge is a much sought-after pretty village on the east of the Isle of Wight and Quiet Corner Cottage is a cosy semi-detached bungalow, perfectly situated just a mile from the ...

  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £533

We are Gold accredited with the Green Tourism Business Scheme.

10 Bayclose is a 2 bedroom self catering apartment with sea views in Freshwater, Isle of Wight
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £547

10 Bayclose

5159

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


Overlooking the gorgeous coastline at Freshwater Bay sits 10 Bayclose, a wonderfully homely apartment perfect for a family getaway to the seaside. With light and airy interiors, sn...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £547

Yardley is a 2 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £562

Yardley

3697

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


Yardley is a charming Victorian cottage, set in the centre of the pretty sailing village of Seaview. The beach and local shops are only a few minutes from your doorstep making this...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £562

Modwena is a 3 bedroom self catering cottage near the sea in Yarmouth, Isle of Wight.
  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £572 *

Modwena

4468

3 bedroom self catering cottage near the sea in Yarmouth, Isle of Wight.


This gorgeous three bedroom cottage is in the picturesque town of Yarmouth just a few minutes' walk from the village centre and historic pier. Located on the west coast of the Isla...

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

7 nights from £572 *

Spinnakers is a 2 bedroom, dog friendly holiday cottage near the beach in Yarmouth, Isle of Wight.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £599

Spinnakers

3659

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


A really lovely little bungalow, holding true to its seaside location with a nautical feel to the interior styling, semi-detached Spinnakers is situated on a small private estate w...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £599

View
  • 50% off

    6 Dec 2024 - 13 Dec 2024

    £599.00 £299.50

The Dairy is a 2 bedroom, dog friendly cottage near the beach near Brighstone, Isle of Wight.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £600

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 £600

The Stables  is a 2 bedroom, dog friendly self catering cottage near Brighstone, Isle of Wight.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £603

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 £603

Readymade beds and fluffy towels; this simple but appreciated welcome is standard with us.

The Pigsty is a 2 bedroom, dog friendly cottage near the beach near Brighstone, Isle of Wight.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £603

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 £603

Lucaya is a 4 bedroom self catering cottage near the beach in Ryde, Isle of Wight.
  • Sleeps 8 + cot
  • No pets
  • Changeover Sat

7 nights from £615 *

Lucaya

3621

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


Welcome to Lucaya, a smart town house for eight set over three floors, a great space with a pretty enclosed rear patio and lawn, the ideal stay for a family looking for a seaside b...

  • Sleeps 8 + cot
  • No pets
  • Changeover Sat

7 nights from £615 *

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