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, rural 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, and just a short walk from the beach and shops. Delightfully renovated, this co...

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

Price per week £415 - £625

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

Price per week £419 - £609

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, and offers comfortable accommodation for couples and families. Enjoy al fresco ...

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

Price per week £429 - £633

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


Decorated with vibrant hues, this charming and spacious ground floor apartment offers cosy and comfortable accommodation in the picturesque village of Seaview. With pretty gardens ...

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

Price per week £443 - £656

View
  • 40% off

    27 Jul 2018 - 3 Aug 2018

    £780.00 £468.00

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

2 bedroom, dog friendly cottage near the beach in 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

Price per week £448 - £666

2 bedroom, dog friendly holiday cottage near the beach in 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

Price per week £448 - £666

View
  • 20% off

    21 Jul 2018 - 28 Jul 2018

    £780.00 £624.00

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


6 St Joseph’s has stunning panoramic sea views, which you can sit and admire from the balcony, living room and master bedroom! Ideally positioned between Bonchurch and Ventnor this...

  • Sleeps 4 + 2 cots
  • Regret no pets
  • Changeover Fri

Price per week £470 - £695

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


Nestled in the stunning countryside on the south west coast of the Island with far reaching sea views over the Military Road, this gorgeously converted barn is the perfect holiday ...

  • Sleeps 4 + 2 cots
  • Regret no pets
  • Changeover Fri

Price per week £475 - £710

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


One of two beautifully converted barns right in the heart of the Island's Area of Outstanding Natural Beauty. Equipped and decorated to a high standard mixing the charming features...

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

Price per week £475 - £710

2 bedroom, dog friendly houseboat on the sea in Bembridge Harbour, Isle of Wight.


For a holiday with a difference this is it! Situated on a private pontoon in Bembridge Harbour, you will have fond memories of your time on this unique floating home for years to c...

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

Price per week £496 - £730

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