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 58 May half-term cottages on the Isle of Wight

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

7 nights from £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

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

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

  • 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 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £750

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

7 nights from £750

  • 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

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

7 nights from £1086

2 bedroom, rural holiday apartment near the beach in Freshwater, Isle of Wight


This beautiful contemporary apartment is literally perched above the beach, offering stunning views of the picturesque Freshwater Bay. Extremely well appointed, the apartment offer...

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

7 nights from £1086

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

7 nights from £632

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


1 The Saltings is a three-bedroom, lower ground floor apartment boasting a lovely beachfront location. It would ideally suit a family with children keen to enjoy the delights of th...

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

7 nights from £632

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

7 nights from £672

2 bedroom self catering cottage at Island Harbour, near Newport.


Spring Tide is a delightful holiday cottage situated in a small development at Island Harbour Marina on the banks of the River Medina. The marina is set in a beautiful secluded val...

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

7 nights from £672

Each and every one of our cottages is fully equipped with everything you’ll need on holiday.

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

7 nights from £758

3 bedroom self catering cottage near the beach in Brook.


September Cottage is an excellent, family-friendly holiday home with an expansive, attractive kitchen and good-sized kitchen, sitting and dining areas. It's easy to imagine curling...

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

7 nights from £758

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

7 nights from £975

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


An incredibly stylish three bedroom ground floor apartment ideally located a few minutes' walk from the village of Seaview and the beach. A lovely large entrance hall centrally fra...

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

7 nights from £975

Loading more