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 36 May half-term cottages on the Isle of Wight

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

7 nights from £391

Berryl Mead View

3906

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 £391

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

7 nights from £420

Faithfull Cottage

3600

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 £420

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

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

7 nights from £427

2 Bermuda

3517

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


2 Bermuda is a lovely, neutrally decorated first floor apartment with wonderful views across the Solent, a balcony for al fresco drinks and a pretty garden. With both the beach and...

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

7 nights from £427

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

7 nights from £452

5 Sandpipers

3557

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


5 Sandpipers is a well-equipped, modern house set within a small development in the heart of Seaview. It offers comfortable accommodation for a couple or small family. The livi...

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

7 nights from £452

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

7 nights from £468

6 Pier View Court

3559

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


6 Pier View Court, perfectly located right on the seafront at Ryde, is a modern, well presented second floor apartment, tastefully decorated and furnished to a high standard. Relax...

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

7 nights from £468

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £473

2 Bagwich Barn

3516

2 bedroom, dog friendly holiday cottage in a rural setting close to Godshill, Isle of Wight


A barn conversion in a rural setting, you'll enjoy a feeling of peace from the moment you step inside this lovely retreat, with its exposed beams and rustic decor. Sitting with...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £473

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

7 nights from £512

Spindrift

4437

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


This gorgeous two bedroom terraced cottage is a few minutes from the beach, right in the heart of Seaview village, offering an ideal holiday bolthole on the picturesque Isle of Wig...

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

7 nights from £512

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

7 nights from £560

Yardley

3697

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


Yardley is a charming Victorian cottage, set in the centre of the pretty sailing village of Seaview. The beach and local shops are only a few minutes from your doorstep making this...

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

7 nights from £560

Readymade beds and fluffy towels; this simple but appreciated welcome is standard with us.

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

7 nights from £575

1 Starboard House

3507

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 the cenre of Seaview village and enjoys unin...

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

7 nights from £575

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

7 nights from £595

Winkle Cottage

4395

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


This gorgeous terraced cottage new to our portfolio for 2020 is situated in the Conservation Area of the old town of Cowes, is just a few minutes walk from the centre of town. Offe...

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

7 nights from £595

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