May Day Bank Holiday on the Isle of Wight
With May Day bank holiday approaching, why not treat yourself to an idyllic retreat on the Isle of Wight? At Classic Cottages we have a range of holiday cottages offering wide variety and consistent quality. Take a look through our collection and let your imagination run away with ideas and plans for a luxury getaway; the Isle of Wight is beckoning. Read more
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.86 Isle of Wight cottages for May Day bank holiday
7 nights from £422 booking fees included
1 Harrow Cottages
46421 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...
7 nights from £422
7 nights from £651 booking fees included
The Cattle Byre
45352 bedroom, dog friendly self catering cottage near Brighstone, Isle of Wight.
Tucked away in a peaceful rural setting on the west side of the island, The Cattle Byre is a beautifully converted barn that blends rustic charm with modern comfort. Perfect for a ...
7 nights from £651
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7 nights from £477 booking fees included
Cockleshells
38152 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight
Seaview is a wonderful base for an Isle of Wight holiday and Cockleshells sits in the perfect location, just a short stroll from the glorious beach and centre of the village. Situa...
7 nights from £477
7 nights from £477 booking fees included
Sugar Beach
51022 bedroom dog friendly self catering cottage near the beach in Seaview, Isle of Wight
Seaview is a much sought-after charming village on the east of the Isle of Wight, and Sugar Beach is perfectly situated just a stone's throw from the beach and a short stroll away ...
7 nights from £477
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7 nights from £491 booking fees included
Berry Cabin
52862 bedroom, dog friendly, bolthole in Seaview, Isle of Wight.
What a little cutie! Berry Cabin is a delightful bolthole for four guests and one well behaved doggy looking for some summer fun! Surrounded by Hersey nature reserve and countrysid...
7 nights from £491
7 nights from £513 booking fees included
Bay Cottage
61502 bedroom self catering cottage near the beach in Cowes.
Tucked away in the charming village of Gurnard on the northwest coast of the Isle of Wight, this cosy two bedroom cottage offers a relaxed coastal lifestyle, complete with a pretty...
7 nights from £513
7 nights from £529 booking fees included
Faithfull Cottage
36002 bedroom, dog friendly holiday cottage near the beach in St Helens, Isle of Wight.
Faithfull Cottage is a welcoming retreat situated within two miles distance of St Helens village on the Isle of Wight, as well as a gorgeous beach, RSPB Nature Reserve and the vill...
7 nights from £529
7 nights from £573 booking fees included
2 Bermuda
35172 bedroom self catering apartment with sea views in Seaview, Isle of Wight.
Welcome to 2 Bermuda, a rather lovely first floor apartment nestled in the charming village of Seaview, with wonderful views stretching across the Solent - ideal for an unforgettab...
7 nights from £573
7 nights from £585 booking fees included
6 St Josephs
38462 bedroom self catering apartment with sea views in Ventnor, Isle of Wight
6 St Josephs is a top floor apartment with stunning panoramic sea views, which you can admire from the balcony, sitting-room and main bedroom! Ideally positioned between Bonchurch ...
7 nights from £585
7 nights from £612 booking fees included
Quiet Corner Cottage
36462 bedroom, dog friendly holiday cottage near the beach in Bembridge, Isle of Wight.
Bembridge is a much sought-after pretty village on the east of the Isle of Wight and Quiet Corner Cottage is a cosy semi-detached bungalow, perfectly situated just a mile from the ...
7 nights from £612
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.
All around the Isle of Wight, May brings a splash of colour and lots of activity. With spring in its final throes and summer on its way, you can expect a pick up in pace and plenty to look forward. However you envisage your perfect getaway, be it a seaside sanctuary with ocean views, dog-friendly country cottage or spacious retreat big enough for all the family and friends, our collection of 86 Isle of Wight cottages available for May Day bank holiday will capture heart and mind. Pour through our portfolio and let your excitement build, a dream holiday is just around the corner. At Classic Cottages, we pride ourselves on marketing only the highest quality self-catering accommodation on the Isle of Wight. With each property handpicked and personally inspected, you can enjoy the best of the best this May. Secure your cottage today.
