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 60 May half-term cottages on the Isle of Wight
7 nights from £1150
Hillcrest House
42653 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...
7 nights from £1150
7 nights from £1204
10 Shanklin Manor
35113 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...
7 nights from £1204
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10% off
16 Feb 2019 - 23 Feb 2019
£624.48 £562.03
7 nights from £730
30 Seaview Bay
35493 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...
7 nights from £730
7 nights from £785
Pandora Lodge
36423 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...
7 nights from £785
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 £853
Lawn End
36173 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...
7 nights from £853
7 nights from £900
9 Crown Court
41693 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 ...
7 nights from £900
7 nights from £975
6 Seaview House
35633 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...
7 nights from £975
7 nights from £997
Willow Tree Lodge
39493 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 ...
7 nights from £997
7 nights from £1050
Fernsdale
40053 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...
7 nights from £1050
7 nights from £1100
Primrose Cottage
36453 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...
7 nights from £1100
We’re a Visit England Quality Accredited Agency for our high standards in holiday letting.
Quality Accredited Agency
Only the highest quality of accommodation is awarded Visit England accreditation. The assessment takes place over a few days and looks at all of our policies, practices and procedures, making sure we meet a five star standard for our guests.
We set our own standards above and beyond and we’re very proud of this accolade and all it represents.