Isle of Wight Cottages for May Half-Term

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

We have 30 May half-term cottages on the Isle of Wight

The Shack is a 1 bedroom, dog friendly holiday cottage with sea views in Cowes.
  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £975

The Shack

5634

1 bedroom, dog friendly holiday cottage with sea views in Cowes.


Overlooking the waters of the Solent, start your mornings on the front deck admiring the view whilst deciding how to spend your day. Instantly relax into your holiday and breathe i...

  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £975

Driftwood is a 2 bedroom dog friendly luxury retreat with private hot tub.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £808 *

Driftwood

5613

2 bedroom dog friendly luxury retreat with private hot tub.


Whisk yourself away to this pretty retreat on the glorious Isle of Wight, new to the portfolio this spring and perfect for couples, small families and four-legged companions who lo...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £808 *

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

Blakesley Cottage is a 2 bedroom, dog friendly self catering cottage in Godshill, Isle of Wight.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £725

Blakesley Cottage

5565

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


Nestled in the very heart of the Isle of Wight's rolling countryside close to the quintessential English village of Godshill yet just a short drive away from the stunning beaches o...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £725

Bagwich House

  • Sleeps 8 + 2 cots in 2 properties
  • Changeover Sat

7 nights from £1224

Lower Buoys is a 2 bedroom self catering apartment near the beach in Seaview, Isle of Wight.
  • Sleeps 4
  • No pets
  • Changeover Sat

7 nights from £1080

Lower Buoys

5457

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


Looking for buried treasure and an Island adventure? Look no further than this super ground floor, luxuxy apartment in a premier destination in the heart of Seaview. Enjoy beachsid...

  • Sleeps 4
  • No pets
  • Changeover Sat

7 nights from £1080

Forget Me Not Cottage is a 3 bedroom self catering cottage near the beach in Bembridge, Isle of Wight
  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £1135

Forget Me Not Cottage

5167

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


Welcome to the delightfully named Forget Me Not Cottage, a charming three bedroom getaway in the pretty coastal town of Bembridge. With its homely interiors and great location, thi...

  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £1135

Leeway House is a 4 bedroom, dog friendly holiday cottage near the beach in Cowes, Isle of Wight
  • Sleeps 8 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1908

Leeway House

5138

4 bedroom, dog friendly holiday cottage near the beach in Cowes, Isle of Wight


Renowned as home to the largest sailing regatta in the world, Cowes is a pretty seaport town on the north side of the Isle of Wight, with fabulous views over the Solent and a great...

  • Sleeps 8 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1908

Oystercatcher is a 3 bedroom houseboat in Bembridge, Isle of Wight.
  • Sleeps 6
  • No pets
  • Changeover Fri

7 nights from £1327 *

Oystercatcher

4869

3 bedroom houseboat in Bembridge, Isle of Wight.


Set in picturesque Bembridge Harbour with far reaching views out to the Solent, Oystercatcher is a luxurious houseboat, beautifully furnished and just waiting to welcome you on boa...

  • Sleeps 6
  • No pets
  • Changeover Fri

7 nights from £1327 *

Our guests rate us 4.8/5 on Feefo, the independent review site.

Buckland Cabin  is a 1 bedroom cabin near the beach in Seaview, Isle of Wight.
  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £796

Buckland Cabin

4853

1 bedroom cabin near the beach in Seaview, Isle of Wight.


Tucked away just off the High Street in Seaview, this recently renovated and beautifully presented cabin is ideal if you are seeking a romantic hideaway for two. Step inside th...

  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £796

View
  • 15% off

    24 May 2024 - 31 May 2024

    £955.00£811.75

1 Harrow Cottages is a 1 bedroom self catering apartment near the beach in Seaview, Isle of Wight.
  • Sleeps 2 + cot
  • No pets
  • Changeover Sat

7 nights from £429

1 Harrow Cottages

4642

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


This charming first floor apartment is in Nettlestone, just up the hill from Seaview and within walking distance of the beach. Surrounded by countryside there are lovely views from...

  • Sleeps 2 + cot
  • No pets
  • Changeover Sat

7 nights from £429

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