Luxury Cottages in May on the Isle of Wight

Put a spring in your step and stay in a luxury self-catering cottage on the Isle of Wight this May. Whether it's a May half-term holiday, a short break over a May bank holiday or a much-anticipated getaway ahead of the summer crowds, our portfolio of 153 available properties provide an idyllic base. Look forward to adventure, fun and total comfort all with the Isle of Wight's stunning backdrop. Read more

Whoever you want to spend your dream holiday with on the Isle of Wight, be it a solo retreat, family holiday or catch up with friends, the choice is yours. One thing is for certain though: where you want to spend it. At Classic Cottages, we offer the finest quality self-catering accommodation around. With each property carefully selected onto our books, we personally inspect all of our cottages to maintain the highest standards. 

From cosy one-bed retreats to spacious family-friendly properties, we have a wide range of properties ready and waiting to welcome you. Fall in love with a beach-side cottage with spectacular sea views, or luxuriate in a rural retreat with a beautiful garden perfect for long afternoons in the sunshine. Pick a private escape set back away from it all, or choose a bolthole close to all the local amenities. The holiday of your dreams awaits.

May Cottages on the Isle of Wight 

At Classic Cottages, we understand the importance of accommodation in making or breaking your holiday. That's why all of our self-catering cottages have been handpicked; personally inspected to make sure only the best make it onto our books. You needn't worry about cramming everything into your luggage either. Each of our cottages is equipped with a full inventory. Everything from your bed linens to your morning coffee pot to enough crockery is provided, so you needn't worry about a thing. 

Isle of Wight Ferry Booking With 200 ferries daily, our hassle free booking service makes your trip to the island plain sailing

See our range of 153 available cottages in May on the Isle of Wight

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £665

3 bedroom, dog friendly cottage near the beach in East Cowes, Isle of Wight.


This truly lovely holiday home, with a wood-burner, is a great choice whatever the season. 1 Barton Lodge is a beautiful property which has been lovingly restored with your comfort...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £665

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

7 nights from £665

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


The Barn, a linked country cottage with a rustic interior and some exposed wooden beams, is located on the outskirts of Merstone and just minutes from the quaint village of Godshil...

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

7 nights from £665

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

  • Sleeps 6 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £675

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


Located on the corner of Ryde Road, Westbourne is a lovely property ideally placed for Seaview Village and the beach. The village amenities are just a few minute's stroll away and ...

  • Sleeps 6 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £675

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

7 nights from £675

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


Tucked away down a quiet side street in the idyllic village of Seaview, Portholes is a fantastic holiday home just minutes away from the sea. All within walking distance from your ...

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

7 nights from £675

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

7 nights from £675

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


Tucked away in the heart of Seaview village, 6 Seaview House is a charming ground floor apartment within a few minutes’ walk of the beach. It has private parking for two cars and a...

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

7 nights from £675

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

7 nights from £695

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


Primrose Cottage is a fully modernised and beautifully furnished Victorian three bedroom cottage situated just off the green in St Helens and offering everything you might need for...

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

7 nights from £695

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

7 nights from £695

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


1 Harbour Strand is a town house with jaunty decor, attractive furnishings and interesting prints, including some of the owners own artwork. It offers a games-room, with table-tenn...

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

7 nights from £695

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

7 nights from £698

3 bedroom self catering cottage in Whitwell, Isle of Wight


Set in the rural village of Whitwell, less than three miles outside of Ventnor, Willow Tree Lodge would suit a family looking for extra space indoors and out or a couple wanting a ...

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

7 nights from £698

We’re a Visit England Quality Accredited Agency for our high standards in holiday letting.

  • Sleeps 6 + 2 cots
  • Regret no pets
  • Changeover Sat

7 nights from £700

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


This property is a truly idyllic cottage situated in the grounds of a farm, with stunning countryside views and a lovely garden. This is what you would describe as holiday heaven. ...

  • Sleeps 6 + 2 cots
  • Regret no pets
  • Changeover Sat

7 nights from £700

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

7 nights from £720

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


A seaside sanctuary, Shore House is a three-storey beautifully decorated house, with its own private heated swimming pool. Making the most of the far reaching views over the Solent...

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

7 nights from £720

Loading more