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 139 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 139 available cottages in May on the Isle of Wight

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

7 nights from £575

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 both the coastline and village amenities, in fact it is just steps away from a f...

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

7 nights from £575

View
  • 10% off

    29 Mar 2019 - 5 Apr 2019

    £510.00 £459.00

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

7 nights from £590

3 bedroom self catering apartment near the beach in Seaview.


With a comfortable interior, an unbeatable location, manicured grounds and the beach within easy reach, 3 Springfield Court has it all. This delightful holiday home would suit a fa...

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

7 nights from £590

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

7 nights from £592

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

7 nights from £592

View
  • 20% off

    29 Mar 2019 - 5 Apr 2019

    £529.98 £423.98

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

7 nights from £593

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


A hidden gem tucked away on Bluett Avenue in the peaceful Victorian village of Seaview, Lawn End makes great use of accent colours in its interior decor presenting a beautiful holi...

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

7 nights from £593

View
  • 10% off

    29 Mar 2019 - 5 Apr 2019

    £530.61 £477.55

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

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £609

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

7 nights from £609

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £610

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


Welcome to Solent Peek, a lovely comfortable home in Totland on the West Coast of the Island. As the name suggests, there is sea view from the first floor master bedroom and it is ...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £610

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

7 nights from £610

3 bedroom self catering apartment near the beach in Seaview.


Perched right on the waterfront opposite Seaview beach, 3 Quay Rocks has unrivalled views of the attractive seafront and beyond, out to the ships passing by on the Solent. The apar...

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

7 nights from £610

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

7 nights from £630

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


This charming cottage is tucked away down an unmade road just off Bembridge Harbour, within walking distance of Bembridge village centre. The front and rear gardens of Old Railway ...

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

7 nights from £630

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

7 nights from £643

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


Rose Villa is a beautifully appointed home in the heart of the village of Yarmouth. It would ideally suit a family or a group of friends traveling together. This spacious prope...

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

7 nights from £643

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

7 nights from £656

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


Trevenna is a thoughtfully designed holiday home in Seaview that really delivers when it comes to space, charm and comfort. It would be ideal for a family or several couples travel...

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

7 nights from £656

We’ve been raising the standards of self catering holidays since 1977.

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