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 137 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 137 available cottages in May on the Isle of Wight

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

7 nights from £392

2 bedroom, dog friendly holiday cottage near the beach in Seaview.


4 Tollgate Cottage is located near Seaview on the Duver - a beach front area that is home to the stunning Hersey Nature Reserve. This cosy cottage would suit a small family or a co...

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

7 nights from £392

  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £393

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


Cockleshells is one of the charming Salterns bungalows situated along the Seaview Duver within a short walk to the Yacht Club and Seaview Village. The new Owner has completely rede...

  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £393

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

7 nights from £395

2 bedroom, dog friendly apartment near the beach in Bembridge, Isle of Wight.


This two bedroom apartment in Bembridge is small but perfectly formed. Lovingly restored by the owners, 53a offers a perfect base for a family with a light and airy double bedroom ...

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

7 nights from £395

View
  • 10% off

    24 May 2019 - 31 May 2019

    £575.05 £517.55

  • Sleeps 4
  • Regret no pets
  • Changeover Fri

7 nights from £399

2 bedroom self catering cottage near the beach in Seaview.


This delightful, stylish seafront bungalow is located in a front row position with wonderful views of the Solent and the beach is practically on the doorstep. Days at the seaside, ...

  • Sleeps 4
  • Regret no pets
  • Changeover Fri

7 nights from £399

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

  • Sleeps 4
  • Regret no pets
  • Changeover Fri

7 nights from £400

2 bedroom, rural self catering apartment near Ventnor, Isle of Wight


Situated on the south coast of the Island, Sea Thrift is a pleasant ground floor apartment set in the ground of lovely gardens. With two delightful double bedrooms, both with en su...

  • Sleeps 4
  • Regret no pets
  • Changeover Fri

7 nights from £400

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £400

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


23 Tollgate Cottages is a comfortably furnished beach bungalow located in a small, gated waterside development on the edge of Seaview, within walking distance to the shops and cafe...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £400

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

7 nights from £410

2 bedroom self catering apartment with sea views in Seaview.


Not far from the sea you will find 2 Bermuda, a bright, neutrally decorated flat that is perfect for a family with children or a couple. The location is what makes this flat so spe...

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

7 nights from £410

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

7 nights from £415

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. The beach and local shops are only a few minutes from your doorstep making this...

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

7 nights from £415

View
  • 15% off

    24 May 2019 - 31 May 2019

    £625.29 £531.50

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

7 nights from £419

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 £419

  • 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 farms milking parlour, Dairy Cottage is a light and airy ground floor cottage with plenty of charm throughout. With a double bedroom with pleasant views across the f...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £428

We are Gold accredited with the Green Tourism Business Scheme.

Loading more