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. 

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 61 May half-term cottages on the Isle of Wight

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 £695

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

Price per week £698

2 bedroom, dog friendly self catering cottage in Godshill, Isle of Wight


Bagwich Barn Cottage is located in a stunning setting within the grounds of the main house and with two other barns available for larger parties. A charming sun-room to the front o...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

Price per week £700

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

Price per week £704

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  • 20% off

    31 Aug 2018 - 7 Sep 2018

    £578.52 £463.20

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 £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 £710

Don’t miss out; reserve your favourite 2019 holiday cottage for just £30

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

Price per week £725

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 £730

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


With an interesting history and dating from 1852, Trevessa was once a fishing cottage and overlooks the sea. The sitting-room, dining-room and both bedrooms have beautiful sea view...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £746

2 bedroom self catering apartment near the beach in Seaview.


2 Springfield Court is an exclusive, ground floor apartment set within a gated development. Boasting eight acres of shared grounds, guests can enjoy use of the extensive grounds, h...

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

Price per week £844

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