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 2 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £380

1 Harrow Cottages

4642

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


This charming first floor apartment is in Nettlestone, just up the hill from Seaview and within walking distance of the beach. Surrounded by countryside there are lovely views from...

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

7 nights from £380

  • Sleeps 2
  • Regret no pets
  • Changeover Sat

7 nights from £639

Oceanix

4900

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


A beautifully located top floor apartment in the heart of Ventnor, Oceanix provides the perfect sea-side getaway for your next Isle of Wight holiday. The property has been thoug...

  • Sleeps 2
  • Regret no pets
  • Changeover Sat

7 nights from £639

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

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

7 nights from £445

Cockleshells

3815

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


Cockleshells is one of the charming Salterns bungalows situated along the Seaview Duver within a short walk to the Yacht Club and Seaview Village. The accommodation offers a double...

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

7 nights from £445

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £481

Dairy Cottage

3912

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


Originally the farm's milking parlour, Dairy Cottage is a light and airy single-storey cottage with plenty of charm throughout. Mattingly Farm is made up of three barns in total Da...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £481

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £481

Orchard Cottage

3936

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


Originally the farm's milking parlour, this delightful semi-detached cottage sleeping four is the perfect cottage to spend quality time together as a family in a stunning rural loc...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £481

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £561

2 Bagwich Barn

3516

2 bedroom, dog friendly holiday cottage in a rural setting close to Godshill, Isle of Wight


A barn conversion in a rural setting, you'll enjoy a feeling of peace from the moment you step inside this lovely retreat, with its exposed beams and rustic decor. Sitting with...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £561

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

7 nights from £571

Fir Cottage

3602

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


Located in a quiet lane a few steps from St Helens village green, Fir Cottage is a freshly decorated, refurbished Victorian semi-detached house, complete with all modern amenities....

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

7 nights from £571

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

7 nights from £583

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
  • Regret no pets
  • Changeover Fri

7 nights from £583

We’re here to help you find your perfect place to stay 7 days a week.

  • Sleeps 4
  • Regret no pets
  • Changeover Sat

7 nights from £597

1 Starboard House

3507

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


If you're looking for a property that's practically on the beach, then this is it! 1 Starboard House perches just opposite the beach in the centre of Seaview village and enjoys uni...

  • Sleeps 4
  • Regret no pets
  • Changeover Sat

7 nights from £597

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

7 nights from £632

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 £632

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