Isle of Wight Cottages for May Half-Term

Blue skies, warm sunshine and long days filled with whatever you please. May half-term holidays are an excellent way to welcome summer and slip into a relaxed rhythm. Gather the family, hop in the car and arrive at your own private retreat. With our self-catering cottages you can enjoy all the Isle of Wight has to offer from your very own home-from-home. Read more

Travel solo, have a romantic getaway, or take advantage of some true family time and have a half-term to remember. Our self-catering cottages offer an idyllic retreat from the chaos of everyday life, so welcome in the summer and kick back. Many of our cottages are dog-friendly too, which means no one gets left behind this May half-term. 

Self-Catering Cottages on the Isle of Wight this May Half-Term

Whether you're planning a much-anticipated holiday or are looking for a spontaneous last-minute break to spend your May half-term on the Isle of Wight, we will help you to find the holiday cottage of your dreams. At Classic Cottages, we pride ourselves on marketing only the finest quality holiday cottages on the Isle of Wight. Each of our cottages is handpicked; personally inspected and fully equipped to ensure your holiday is the best it can be. Every step of the way, we offer help and support so that your whole experience is as smooth and relaxed as possible. 

If you have any questions, don't hesitate to get in touch

Isle of Wight Ferry Booking With 200 ferries daily, our hassle free booking service makes your trip to the island plain sailing

We have 38 May half-term cottages on the Isle of Wight

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

7 nights from £587

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 £587

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

7 nights from £625

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 £625

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

7 nights from £648

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


Located in the cosmopolitan town of Ventnor in a Victorian town house, Seascape is a modern two bedroom apartment with spectacular sea views along the coastline. It offers contempo...

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

7 nights from £648

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

7 nights from £675

2 bedroom self catering cottage with sea views in Seaview.


North View is a wonderful holiday hideaway just on the outskirts of Seaview with sea views across the Solent from the kitchen/dining-room and first floor bedrooms. Set back from th...

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

7 nights from £675

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

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £698

2 bedroom, dog friendly self catering cottage near Yarmouth, Isle of Wight


If you are looking for a traditional cottage, look no further than Blakes Barn. Constructed from Island stone, the charm starts outside Blakes Barn with the beautiful brick work, t...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £698

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

7 nights from £704

2 bedroom, dog friendly holiday apartment with sea views in Ventnor, Isle of Wight.


Gilmerton is a charming and spacious apartment, beautifully decorated, and located on the outskirts of the vibrant town of Ventnor. The house is built into the hill so this first f...

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

7 nights from £704

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

7 nights from £710

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

7 nights from £710

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

7 nights from £725

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


If you're looking for a property that's practically on the beach, then this is it! 1 Starboard House perches just opposite the beach in central Seaview and enjoys uninterrupted sea...

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

7 nights from £725

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

7 nights from £738

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


Venice Lodge is a Georgian cottage located in a quiet residential area of the popular seaside town of Ryde. This is a unique house that you will not soon forget. If you long for th...

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

7 nights from £738

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

7 nights from £754

2 bedroom self catering apartment with sea views in Ventnor.


With sea views from the terrace and fresh, modern décor throughout, 2 St Josephs is a holiday maker's home-from-home. It is the perfect get-away for a small family, a couple or two...

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

7 nights from £754

We’re a Visit England Quality Accredited Agency for our high standards in holiday letting.

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