Summer Holiday Cottages on the Isle of Wight
A summer on the Isle of Wight in a Classic cottage combines the ultimate holiday experience with luxury self-catering accommodation. Head out and about during the day and explore all that the Isle of Wight has to offer, and in the evening return to your own private paradise. For an unforgettable summer, we have 97 holiday homes available for you to rent. Read more
The summer is finally here! Now, what to do with it? Why not escape for a week or two by hopping on a ferry and heading to the island? It instantly feels like you're 'getting away from it all' when you travel by boat! Explore the incredible coastline, dip in the sea for a swim or two and explore all corners the Isle of Wight has to offer for a perfect self catering holiday this summer.
Whatever you are looking for in a summer break, choose the flexibility a holiday cottage on the Isle of Wight will give you.
97 self-catering cottages for the summer holidays on the Isle of Wight
7 nights from £900
The Clock House
45592 bedroom self catering cottage near the beach in Yaverland, Isle of Wight.
This beautifully decorated converted former stable, in the grounds of the Old Rectory in Yaverland just outside Bembridge, is a real gem. The owner has created a stylish and indivi...
7 nights from £900
7 nights from £1350
Culver View
45554 bedroom self catering cottage near the beach in St Helens, Isle of Wight.
Located down a single-track road off the lower Green in the village of St Helens, Culver View has a beautiful garden and far reaching views over Culver Downs. A spacious and light ...
7 nights from £1350
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 £2600
Redworth
45415 bedroom self catering home near the beach in Bembridge, Isle of Wight.
This impressive five bedroom house is located on Ducie Avenue, a charming unmade road leading to the beach, in the village of Bembridge. Located within a few minutes walk to the lo...
7 nights from £2600
7 nights from £675
The Stables
45372 bedroom, dog friendly self catering cottage near Brighstone, Isle eof Wight.
The Stables is light and airy throughout with two bedrooms, a king-size double and a twin. The open plan living-room with kitchen and dining areas is warm and inviting, with doors ...
7 nights from £675
Kingston Barns
7 nights from £2700
7 nights from £675
The Pigsty
45382 bedroom, dog friendly cottage near the beach near Brighstone, Isle of Wight.
The Pigsty is a detached barn with parking for two cars and two private seating areas alongwith a spacious communal area. There are two bedrooms, a double and a twin, each beau...
7 nights from £675
7 nights from £750
The Dairy
45362 bedroom, dog friendly cottage near the beach near Brighstone, Isle of Wight.
The Dairy is the largest of all four barns and is closest to The Cattle Byre. It has a spacious kitchen and dining area making it a social space for the family to gather and make p...
7 nights from £750
7 nights from £600
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 £600
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 £725
Willow Cottage
45172 bedroom self catering cottage near the beach near Newport, Isle of Wight.
This charming two bedroom cottage is located in the exclusive development of Island Harbour, with a gated entrance and private resident's parking. Willow Cottage has a sitting/dini...
7 nights from £725
7 nights from £614
Spindrift
44372 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
This gorgeous two bedroom terraced cottage is a few minutes from the beach, right in the heart of Seaview village, offering an ideal holiday bolthole on the picturesque Isle of Wig...
7 nights from £614