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 156 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 156 available cottages in May on the Isle of Wight

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


6 Seafield Terrace is a charming terraced cottage set in the pretty village of Seaview. With spacious accommodation spread over three floors, and the beach close at hand, it makes ...

  • Sleeps 9 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

Price per week £795 - £1192

5 bedroom self catering cottage near the beach in Ryde, Isle of Wight.


Middle Lodge is a gorgeous 1860s, stone-built, Victorian holiday home set in a mature enclosed garden on the edge of Ryde on the east of the island. The outside is charmingly perio...

  • Sleeps 9 + cot
  • Regret no pets
  • Changeover Sat

Price per week £907 - £1413

5 bedroom, dog friendly holiday cottage near the beach in Bembridge, Isle of Wight


This is a three-storey house right in the heart of Bembridge village, just opposite the picturesque village church and a few minutes' walk from the shops and restaurants. The prope...

  • Sleeps 9 + cot
  • Dogs welcome
  • Changeover Sat

Price per week £1000 - £1750

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


2 Little Cedars is a sleek and modern property, with a light and clean finish throughout. Split over three floors, and stylishly decorated with luxury furnishings, this delightful ...

  • Sleeps 9 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

Price per week £1138 - £1892

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


This impressive 150 year old Farmhouse sleeps nine and is the perfect location for a fabulous family gathering of all ages. In the breathtaking location of Barton Manor Estate, adj...

  • Sleeps 9 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £1771 - £2719

5 bedroom, dog friendly holiday cottage with sea views in Wootton, Isle of Wight.


Creekside is a fabulous waterfront property that makes a wonderful choice of holiday home at any time of the year. This stunning detached house, set on the banks of Wootton Creek, ...

  • Sleeps 10 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £921 - £1379

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

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


Swift Cottage is a gorgeous, comfortable Edwardian end-of-terrace property, spread over three levels with wooden flooring throughout the kitchen and dining area. The spacious dinin...

  • Sleeps 10 + cot
  • Regret no pets
  • Changeover Fri

Price per week £926 - £1330

4 bedroom, dog friendly holiday cottage near the beach in Bembridge, Isle of Wight


Orchard House is a wonderful property for an extended family looking for a sprawling holiday home near the beach in Bembridge. The downstairs living areas are inviting - no doubt t...

  • Sleeps 10 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

Price per week £1027 - £1575

4 bedroom, rural self catering cottage near the beach in Shanklin, Isle of Wight.


Mountbatten Garden Apartment is a fabulous apartment stylishly furnished with four en suite bedrooms and comes with a private courtyard including a six person hot tub. Vibrantly de...

  • Sleeps 10 + cot
  • Regret no pets
  • Changeover Fri

Price per week £1125 - £1575

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


Mariners is a beautiful beachfront property offering light, spacious, contemporary family accommodation. Tastefully refurbished in recent years, this modern property is spread acro...

  • Sleeps 10 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

Price per week £1130 - £1798

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