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
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 100 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.
With 200 ferries daily, our hassle free booking service makes your trip to the island plain sailing
100 Isle of Wight cottages for May Day bank holiday
7 nights from £590
3 Springfield Court
35473 bedroom self catering apartment near the beach in Seaview.
With a comfortable interior, an unbeatable location, manicured grounds and the beach within easy reach, 3 Springfield Court has it all. This delightful holiday home would suit a fa...
7 nights from £590
7 nights from £592
23 Coastguard Cottage
35343 bedroom self catering cottage near the beach in Bembridge, Isle of Wight.
This gorgeous property is a stylishly converted coastguard cottage and really is a gem. Beautifully decorated throughout, in greys, blues and whites, it is an oasis of calm and has...
7 nights from £592
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 £625
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 £625
7 nights from £630
Old Railway Cottage
39903 bedroom self catering cottage near the beach in Bembridge, Isle of Wight
This charming cottage is tucked away down an unmade road just off Bembridge Harbour, within walking distance of Bembridge village centre. The front and rear gardens of Old Railway ...
7 nights from £630
7 nights from £643
Rose Villa
36493 bedroom, dog friendly holiday cottage near the beach in Yarmouth, Isle of Wight.
Rose Villa is a beautifully appointed home in the heart of the village of Yarmouth. It would ideally suit a family or a group of friends traveling together. This spacious prope...
7 nights from £643
7 nights from £665
The Barn
36633 bedroom, rural self catering cottage near the beach in Merstone, Isle of Wight.
The Barn, a linked country cottage with a rustic interior and some exposed wooden beams, is located on the outskirts of Merstone and just minutes from the quaint village of Godshil...
7 nights from £665
7 nights from £675
Portholes
40073 bedroom self catering cottage near the beach in Seaview, Isle of Wight
Tucked away down a quiet side street in the idyllic village of Seaview, Portholes is a fantastic holiday home just minutes away from the sea. All within walking distance from your ...
7 nights from £675
7 nights from £695
1 Harbour Strand
35053 bedroom self catering cottage near the beach in Bembridge, Isle of Wight.
1 Harbour Strand is a town house with jaunty decor, attractive furnishings and interesting prints, including some of the owners own artwork. It offers a games-room, with table-tenn...
7 nights from £695
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.
7 nights from £700
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 £700
7 nights from £725
Henley House
39223 bedroom self catering cottage near the beach in Ryde, Isle of Wight
This lovely and well-presented detached house is just moments away from the beautiful golden beaches of Ryde and mainland transport links, creating a perfect location for a base fo...
7 nights from £725