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.
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
7 nights from £391
Berryl Mead View
39061 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...
7 nights from £391
7 nights from £420
Faithfull Cottage
36002 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...
7 nights from £420
Need more time? Reserve any cottage for up to 24 hours before booking.
24hr no commitment reservations
You can reserve your holiday dates on your favourite cottage for up to 24 hours. You might need to check with other guests in your party or simply consider whether this cottage is right for your holiday, either way we’re happy to give you the time to step away and mull over your options before paying a penny.
We’ll send you a reminder to see if you want it or not so you won’t lose out. Take time to think it over, you don’t have to rush your decision. Have a cup of tea and when you’re ready, hit the button to book your holiday and start looking forward to it.
7 nights from £427
2 Bermuda
35172 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...
7 nights from £427
7 nights from £452
5 Sandpipers
35572 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...
7 nights from £452
7 nights from £468
6 Pier View Court
35592 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...
7 nights from £468
7 nights from £473
2 Bagwich Barn
35162 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...
7 nights from £473
7 nights from £512
Spindrift
44372 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...
7 nights from £512
7 nights from £560
Yardley
36972 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...
7 nights from £560
Readymade beds and fluffy towels; this simple but appreciated welcome is standard with us.
Towels and readymade beds
All of our cottages provide bed linen and towels as standard, with a change of bedding included for holidays of two weeks or more. You’ll also find a fresh change of towels for each week (for in the house only, please bring your own for the beach) and tea towels a-plenty.
The beds will be readymade and waiting for you on arrival so you can simply sink into comfort and relax straight into your holiday.
7 nights from £575
1 Starboard House
35072 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...
7 nights from £575
7 nights from £595
Winkle Cottage
43952 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...
7 nights from £595