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 39 May half-term cottages on the Isle of Wight
7 nights from £414
Mariners Cove
36281 bedroom self catering apartment near the beach in Bembridge, Isle of Wight.
This charming one bedroom apartment forms part of a country house, set around a shared Spanish-style courtyard, just outside the bustling village of Bembridge. You can enjoy the ev...
7 nights from £414
7 nights from £507
Little Barn Retreat
41871 bedroom, rural self catering cottage in Newport, Isle of Wight
This absolutely gorgeous barn conversion is the perfect place for a couple's holiday, located on the Durton Farm Estate in the centre of the Island. Lovingly refurbished by the own...
7 nights from £507
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 £534
Smugglers’ Run
39452 bedroom, dog-friendly holiday cottage with sea views in East Cowes, Isle of Wight
Smugglers' Run is a waterside property overlooking the River Medina and across to the sailing town of Cowes. It would suit a family or a couple in need of a little extra space. ...
7 nights from £534
7 nights from £566
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 £566
7 nights from £573
Orchard Cottage
39362 bedroom, dog friendly self catering cottage near Yarmouth, Isle of Wight
Originally the farm's milking parlour, this delightful cottage sleeping four is the perfect cottage to spend quality time together as a family in a stunning rural location. Located...
7 nights from £573
7 nights from £573
Dairy Cottage
39122 bedroom, dog friendly self catering cottage near Yarmouth, Isle of Wight
Originally the farms milking parlour, Dairy Cottage is a light and airy ground floor cottage with plenty of charm throughout. With a double bedroom with pleasant views across the f...
7 nights from £573
7 nights from £599
2 Bermuda
35172 bedroom self catering apartment with sea views in Seaview.
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 £599
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10% off
13 Jul 2019 - 20 Jul 2019
£586.63 £527.97
7 nights from £655
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 sitt...
7 nights from £655
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10% off
12 Jul 2019 - 19 Jul 2019
£633.32 £569.99
Arrive at your handpicked holiday home safe in the knowledge it’s been fully inspected.
Quality inspections
We check our holiday homes to ensure that everything is up to our high standards for your holiday, from provision of our above standard minimum inventory to how fluffy the towels are, we make sure you’ll have a comfortable stay.
Hardworking teams of housekeepers will have the place spick and span, ready for your arrival, so when you get there you can just relax.
7 nights from £686
1 Bagwich Barn
35012 bedroom, dog friendly cottage in a rural setting close to Godshill, Isle of Wight.
A barn conversion, in a rural setting, with a welcoming, rustic feel to it, 1 Bagwich Barn offers an ideal base in the middle of the The Isle of Wight, from which to explore north ...
7 nights from £686
7 nights from £686
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 within t...
7 nights from £686