85 Isle of Wight cottages for May Day bank holiday
7 nights from £809 booking fees included
Valdora
49593 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
Perfectly situated in the heart of the charming village of Seaview, Valdora is a gorgeous holiday retreat, beautifully styled to offer the very best in contemporary living. Seaview...
7 nights from £809
7 nights from £810 booking fees included
Blackberries
35833 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
A warm Isle of Wight welcome awaits you at Blackberries, a pretty coastal cottage which offers a peaceful escape for families, small groups or couples alike, in the delightful sail...
7 nights from £810
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20% off
12 Sep 2026 - 19 Sep 2026
From £1180.00 £956.60 booking fees included
Choose from our exclusive collection at the best prices with real time availability.
Exclusive cottage collections
Our calendars show live availability, so if your pick of dates are available, you can reserve them safe in the knowledge that they won’t get sold anywhere else.
It can be unpredictable using aggregator websites that collect up information from across multiple websites. Our website stands alone, so you know what to expect and what you will get, for the best price. You won’t find this collection of cottages anywhere else, so pick your perfect place to stay from our exclusive portfolio.
7 nights from £815 booking fees included
Trevenna
36863 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
Tucked away in a quiet area of Seaview and perfectly situated just a short stroll from the pretty beach and charming village centre, Trevenna is a beautifully furnished, detached h...
7 nights from £815
7 nights from £851 booking fees included
Wickings
61013 bedroom, dog friendly holiday cottage near the beach in Ventnor.
Nestled in the sheltered seaside town of Ventnor, blessed with its own gentle microclimate, this wonderfully welcoming and peaceful retreat is perfect for relaxing, unwinding and s...
7 nights from £851
7 nights from £860 booking fees included
Beggars Roost
43463 bedroom self catering apartment with sea views in Seaview, Isle of Wight
This gorgeous first floor apartment in the heart of Seaview village is perfectly placed to reach everything within a few minutes' walk. The seafront is just around the corner, a po...
7 nights from £860
7 nights from £871 booking fees included
Longdown Hall
43863 bedroom self catering cottage with sea views in Ventnor, Isle of Wight
A stunning property in Ventnor on the southern tip of the Island, with the most sensational 180 degree sea views from the sun-drenched patio. Relax with your breakfast in the sunsh...
7 nights from £871
7 nights from £916 booking fees included
Old Bembridge House
47913 bedroom, dog friendly holiday cottage near the beach in Bembridge, Isle of Wight.
Perfectly located just moments away from the beach and pretty harbour, Old Bembridge House has all the makings of the perfect holiday idyll on the Isle of Wight. Laid across three-...
7 nights from £916
7 nights from £961 booking fees included
Fenders
59873 bedroom, dog friendly cottage near the beach in Totland.
Your memorable Isle of Wight coastal escape awaits at Fenders, a beautifully appointed single-storey retreat, situated just moments from the picturesque beach at Totland Bay. Tucke...
7 nights from £961
We’re here to help you find your perfect place to stay 7 days a week.
Open 7 days a week
Call our office on 01326 555555, email hello@classic.co.uk or click on the live chat button in the bottom right of the screen to talk directly to someone who can help with choosing your holiday. If you have any questions or need a hand with the booking process, we’re happy to help.
After booking your holiday with us, you’ll receive your holiday details two weeks before your holiday. This also includes our emergency out of hours phone number for when the office is closed, so we’re never more than a phone call away!
7 nights from £971 booking fees included
Underwood Cabin
49953 bedroom, dog friendly self catering cottage near Yarmouth, Isle of Wight.
Nestled next to St Hubert's Lodge surrounded by tranquil woodlands and green pastures, Underwood Cabin is a delightful rural retreat, perfectly situated on the edge of the Isle of ...
7 nights from £971
7 nights from £1051 booking fees included
Oak Tree Cottage
42123 bedroom self catering cottage with sea views in Seaview, Isle of Wight
With gorgeous views over the Solent and the beach just a few steps away, Oak Tree Cottage is a delightful reverse level holiday home situated a short stroll from the village centre...
7 nights from £1051
