Isle of Wights 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 27 May half-term cottages on the Isle of Wight

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

pretty 2 bedroom apartment in Yarmouth town centre, Isle of Wight


Located in the heart of the historic port town of Yarmouth, Harbour Life is perfectly situated within easy reach of the Wightlink ferry and public transport and just moments away f...

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

Price per week £713

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  • 20% off

    6 Jul 2018 - 13 Jul 2018

    £713.39 £570.71

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. This spacious ground floor apartment is ideally situated betw...

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

Price per week £754

2 bedroom, holiday cottage near the beach in St Helens, Isle of Wight.


Hill Farm Lodge with its huge garden offers you plenty of room to stretch your legs or the children to kick a ball! The only steps are but a few to the front door, leading on to an...

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

Price per week £865

Dogs go free on holidays starting between 29th June to 5th July.

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


10 Springfield Court is a wonderful, second floor apartment set within eight acres of communal grounds. The property also benefits from the shared use of an outdoor heated swimming...

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

Price per week £888

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


4A Ship House, an attractive townhouse positioned right in the middle of Seaview, is perfect for a family looking for a coastal break. 'Ship shape' in presentation, the fantastic t...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Fri

Price per week £653

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


This charming first floor apartment is laid over two floors and situated right in the heart of Seaview village, tucked away down a quiet side street called Rope Walk, so called as ...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

Price per week £810

3 bedroom, dog friendly self catering cottage in Ventnor.


This gorgeous stone cottage is nestled in a wonderful countryside location in the central south of the Island, a short distance from the coastal town of Ventnor. Situated at the en...

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Sat

Price per week £900

3 bedroom, rural self catering apartment near the beach near Newport, Isle of Wight


This stunning barn conversion is located just outside the picturesque village of Chillerton, in the heart of the Island’s farming community between Newport and Chale. The outlook o...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Fri

Price per week £950

3 bedroom self catering apartment with sea views in Seaview.


They say location is everything, and this property does not disappoint! Situated on the first floor, 2 Quay Rocks is a light-filled, modestly furnished apartment with a balcony, of...

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

Price per week £795

Choose from our exclusive collection at the best prices with real time availability.

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