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 60 May half-term cottages on the Isle of Wight

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

7 nights from £1150

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


A very charming house overlooking The Green in the picturesque village of St Helens, on the east side of the Island, within a short and scenic walk to the beach. A footpath startin...

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

7 nights from £1150

  • Sleeps 5
  • Regret no pets
  • Changeover Sat

7 nights from £1204

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


Dating back to 1863 and converted in 2011, this superb two-storey apartment is located on the outskirts of Shanklin. 10 Shanklin Manor has an elegant, monochrome interior and the u...

  • Sleeps 5
  • Regret no pets
  • Changeover Sat

7 nights from £1204

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  • 10% off

    16 Feb 2019 - 23 Feb 2019

    £624.48 £562.03

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

7 nights from £730

3 bedroom holiday cottage near the beach in Seaview, Isle of Wight.


30 Seaview Bay is a lovely three bedroom apartment set over two levels, offering sea views from the master bedroom balcony. Doors from the sitting-room lead to a decked area and pr...

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

7 nights from £730

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

7 nights from £785

3 bedroom self catering apartment near the beach in Seaview.


Pandora Lodge is a lovely ground floor apartment forming part of a larger Victorian property in central Seaview. With sea views from the sitting-room and large bay windows featured...

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

7 nights from £785

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

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

7 nights from £853

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


A hidden gem tucked away on Bluett Avenue in the peaceful Victorian village of Seaview, Lawn End makes great use of accent colours in its interior decor presenting a beautiful holi...

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

7 nights from £853

  • Sleeps 6
  • Regret no pets
  • Changeover Sat

7 nights from £900

3 bedroom self catering cottage with sea views in Cowes, Isle of Wight.


Right in the heart of the bustling sailing town of Cowes, 9 Crown Court offers great accommodation with a stunning roof terrace boasting uninterrupted views across the rooftops to ...

  • Sleeps 6
  • Regret no pets
  • Changeover Sat

7 nights from £900

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

7 nights from £975

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


Tucked away in the heart of Seaview village, 6 Seaview House is a charming ground floor apartment within a few minutes’ walk of the beach. It has private parking for two cars and a...

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

7 nights from £975

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

7 nights from £997

3 bedroom self catering cottage in Whitwell, Isle of Wight


Set in the rural village of Whitwell, less than three miles outside of Ventnor, Willow Tree Lodge would suit a family looking for extra space indoors and out or a couple wanting a ...

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

7 nights from £997

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

7 nights from £1050

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


Right in the heart of Seaview village, this semi-detached property has been completely renovated, with a Skandi theme, to offer a wonderful place to stay on the Isle of Wight. With...

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

7 nights from £1050

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

7 nights from £1100

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


Primrose Cottage is a fully modernised and beautifully furnished Victorian three bedroom cottage situated just off the green in St Helens and offering everything you might need for...

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

7 nights from £1100

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

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