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 59 May half-term cottages on the Isle of Wight

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £303

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


West Flatlet is situated right in the heart of Seaview village and is perfect for couples looking for a coastal break. This small but cosy and comfortable first floor flat sits at ...

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £303

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £315

1 bedroom self catering apartment with sea views in Seaview, Isle of Wight


This gorgeous top floor, one bedroom apartment has spectacular sea views over the rooftops across the Solent, and just a few minutes from Seaview village and the beach. Newly deco...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £315

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

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £330

1 bedroom self catering apartment near the beach in Shanklin, Isle of Wight.


Located on the first floor of Shanklin Villa, a lovely Victorian property, this small studio apartment packs a punch despite its size. Enjoying beautiful sea views from its elevate...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £330

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £384

1 bedroom self-catering cottage near Ventnor, Isle of Wight


Located in a rural village setting, Berryl Mead View is a delightful home from home cottage with plenty of space. It is well-equipped throughout and has an extremely comfortable li...

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £384

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  • 10% off

    1 Feb 2020 - 8 Feb 2020

    £336.05 £302.40

  • 10% off

    8 Feb 2020 - 15 Feb 2020

    £336.05 £302.40

  • 10% off

    15 Feb 2020 - 22 Feb 2020

    £405.08 £364.50

  • 10% off

    22 Feb 2020 - 29 Feb 2020

    £336.05 £302.40

  • 10% off

    29 Feb 2020 - 7 Mar 2020

    £336.05 £302.40

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £505

1 bedroom self catering apartment near the beach in Shanklin, Isle of Wight.


Sitting within a beautifully converted Victorian villa, The Cadogan Apartment offers a high standard of accommodation for a couple or lone traveller looking for a coastal break. Gu...

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £505

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

7 nights from £711

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


Beginning its life as accommodation for troops during the First World War, The Blue Beach House has undergone many transformations in its time until its present day status as a cha...

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

7 nights from £711

  • Sleeps 3 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £485

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


This beautifully refurbished house is perfectly situated in the heart of Seaview Village, with a lovely decked area to the rear and outdoor seating so you can enjoy dining in the I...

  • Sleeps 3 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £485

  • Sleeps 3 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £505

1 bedroom self catering apartment near the beach in Shanklin, Isle of Wight.


Offering a high standard of accommodation, The Worsley Apartment is a ground floor apartment within Shanklin Villa, a beautifully converted Victorian building. With a separate kitc...

  • Sleeps 3 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £505

Our property managers are local experts who handpick perfect places to stay.

  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £381

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


Faithfull Cottage is a lovingly restored, pretty mid-terrace cottage which enjoys a rear garden and countryside views on the outskirts of St Helens. This comfortable cottage is set...

  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £381

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

7 nights from £385

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


The Lobster Pot is a comfortably furnished beach bungalow located in a small waterside development on the edge of Seaview and next to a nature reserve. This beach bolt hole has dec...

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

7 nights from £385

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