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 46 available properties provide an idyllic base. Look forward to adventure, fun and total comfort all with the Isle of Wight's stunning backdrop. 

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 46 available cottages in May on the Isle of Wight

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

Price per week £445 - £672

2 bedroom, dog friendly holiday apartment near the beach in Shanklin.


Park Lodge Annexe is a beautifully presented lower ground floor apartment within walking distance to the Rylstone Gardens and the Chine. The cliff path is a minute stroll away, lea...

  • Sleeps 5 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Sat

Price per week £464 - £717

3 bedroom self catering cottage near the beach in Brook.


September Cottage is an excellent, family-friendly holiday home with an expansive, attractive kitchen and good-sized kitchen, sitting and dining areas. It's easy to imagine curling...

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

Price per week £507 - £758

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


The location of 40 Trelawny Way, on a quiet residential road in Bembridge, belies its extravagant interior. For those looking for a family home with an interior decorated with arti...

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

Price per week £549 - £915

3 bedroom self catering apartment near the beach in Seaview.


Pandora Lodge is a lovely ground floor apartment forming part of a larger Victorian property in central Seaview. With sea views from the sitting-room and large bay windows featured...

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

Price per week £528 - £785

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


Set in the delightful sailing village of Seaview, Blackberries is a pretty, refurbished cottage which offers a peaceful escape for families, small groups or couples alike. Comforta...

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

Price per week £539 - £801

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

3 bedroom self catering cottage in East Cowes, Isle of Wight


Turnstone is a beautifully designed, newly built town house situated overlooking the River Medina on the north coast of the island and within walking distance of Osborne House. Fro...

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

Price per week £575 - £825

View
  • 20% off

    28 Jul 2018 - 4 Aug 2018

    £995.00 £796.00

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


Nestled in the heart of Seaview village this lovely ground floor apartment is a stone’s throw from the sea front and all the village amenities. Seaview is an idyllic Edwardian reso...

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

Price per week £575 - £850

View
  • 10% off

    27 Jul 2018 - 3 Aug 2018

    £1000.00 £900.00

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


This gorgeous property is a stylishly converted coastguard cottage and really is a gem. Beautifully decorated throughout, in greys, blues and whites, it is an oasis of calm and has...

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

Price per week £592 - £899

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


Formerly the officer's quarters of the coastguard station, 6 Coastguard Cottages has been beautifully decorated and offers a wonderful holiday home in Brook. This period property h...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Sat

Price per week £609 - £903

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