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 88 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 88 available cottages in May on the Isle of Wight

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

7 nights from £402

2 bedroom self catering apartment with sea views in Seaview.


2 Bermuda is a lovely, neutrally decorated first floor apartment with wonderful views across the Solent, a balcony for al fresco drinks and a pretty garden. With both the beach and...

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

7 nights from £402

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

7 nights from £417

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


Newlands is a charming detached cottage located just off the Green, in the picturesque village of St Helens. Its location is very peaceful yet within walking distance to the villag...

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

7 nights from £417

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

7 nights from £426

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


5 Sandpipers is a well-equipped, modern house set within a small development in the heart of Seaview. It offers comfortable accommodation for a couple or small family. The sitt...

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

7 nights from £426

View
  • 10% off

    30 Aug 2019 - 6 Sep 2019

    £500.12 £450.11

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £428

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. The double bedroom with pleasant views across the fa...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £428

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

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £428

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 £428

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £443

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 within t...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £443

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £443

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


A barn conversion, in a rural setting, with a welcoming, rustic feel to it, 1 Bagwich Barn offers an ideal base in the middle of the The Isle of Wight, from which to explore north ...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £443

View
  • 10% off

    15 Sep 2019 - 21 Sep 2019

    £399.00 £359.10

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

7 nights from £463

2 bedroom self catering apartment with sea views in Ryde.


8 Appley Sands is a spacious, purpose built, top floor apartment overlooking the Solent and the award-winning beach at Appley. With en suites to both bedrooms, and comfortable, mod...

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

7 nights from £463

View
  • 20% off

    31 Aug 2019 - 7 Sep 2019

    £602.64 £482.11

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

7 nights from £467

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


This is a wonderfully secluded property with a charming garden and spacious balcony, all within a few minutes from the idyllic Seagrove Bay in Seaview. There are several steps up t...

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

7 nights from £467

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

7 nights from £469

2 bedroom thatched self catering cottage with sea views in Seaview.


If the restorative power of the sea appeals to you, 1 Thatched Cottage, with its uninterrupted views is an ideal holiday home. This 19th century property combines old world charm w...

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

7 nights from £469

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

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