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 53 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.
53 Isle of Wight cottages for May Day bank holiday
7 nights from £340
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 £340
7 nights from £401
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 £401
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 £500
The Cattle Byre
45352 bedroom, dog friendly self catering cottage near Brighstone, Isle of Wight.
The Cattle Byre has accommodation for three guests across two bedrooms, a double and a single. It has two private outdoor seating areas, the rear enclosed garden can only be access...
7 nights from £500
7 nights from £402
Bagwich Barn Cottage
40552 bedroom, dog friendly self catering cottage in a rural setting close to Godshill, Isle of Wight
Bagwich Barn Cottage is located in a stunning setting within the grounds of the main house and with two other barns available for larger parties. A charming sun-room to the front o...
7 nights from £402
7 nights from £403
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 £403
7 nights from £438
Dairy Cottage
39122 bedroom, dog friendly self catering cottage near Yarmouth, Isle of Wight
Originally the farm's milking parlour, Dairy Cottage is a light and airy single-storey cottage with plenty of charm throughout. Mattingly Farm is made up of three barns in total Da...
7 nights from £438
7 nights from £438
Orchard Cottage
39362 bedroom, dog friendly self catering cottage near Yarmouth, Isle of Wight
Originally the farm's milking parlour, this delightful semi-detached cottage sleeping four is the perfect cottage to spend quality time together as a family in a stunning rural loc...
7 nights from £438
7 nights from £494
Blakes Barn
39072 bedroom, dog friendly self catering cottage near Yarmouth, Isle of Wight
If you are looking for a traditional cottage, look no further than Blakes Barn. Mattingly Farm is made up of three barns in total, Blakes Barn, Dairy Cottage (3912), and Orchard Co...
7 nights from £494
Our property managers are local experts who handpick perfect places to stay.
Local experts
We scour the coast and country to winkle out bits worth sharing with you, the best properties in lovely locations. While we’re out and about, we gather together the best things to do so that you can start planning your holiday as soon as you’ve booked.
The ‘Explore Nearby’ tab on our cottage pages show what’s nearby along with relevant articles from our holiday guides from Notes and Stories, where you’ll find hand-written experiences of outings across the South and West, from dog-friendly pubs on the Isle of Wight to free things to do in south Devon and everything in between.
7 nights from £500
Yardley
36972 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
Yardley is a charming Victorian cottage, set in the centre of the pretty sailing village of Seaview. The beach and local shops are only a few minutes from your doorstep making this...
7 nights from £500
7 nights from £512
Upton View
43502 bedroom self catering cottage near the beach in Seaview, Isle of Wight
Upton View is a lovely cottage on the outskirts of Seaview with double doors opening out from the dining-area to a gorgeous garden and, with outdoor seating, you can while away you...
7 nights from £512