Summer Holiday Cottages on the Isle of Wight
A summer on the Isle of Wight in a Classic cottage is pretty hard to beat when it comes to finding your British summer holiday away. So why not 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 106 holiday homes available for you to rent. Read more Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.
106 self-catering cottages for the summer holidays on the Isle of Wight
7 nights from £1386
Pucks Oak
56984 bedroom, dog friendly holiday cottage with sea views in Seaview.
Within moments of the seafront at Seaview, with off-street parking and a lovely garden, semi-detached Pucks Oak is a great home-from-home to enjoy with friends and family. With the...
7 nights from £1386
7 nights from £496
The Studio
57531 bedroom, dog friendly, cosy cottage near Ryde.
Whether you seek relaxation or adventure on the Isle of Wight, The Studio provides the most welcoming modern-rustic retreat to experience the best of natural beauty and contemporar...
7 nights from £496
The Old Dairy
7 nights from £1406
7 nights from £1040
Bentinck
57243 bedroom cottage near the beach in Ventnor.
With everything you could wish for on your doorstep for a blissful Isle of Wight holiday experience with family or friends, Bentinck is a great base to explore all that this Island...
7 nights from £1040
7 nights from £1329
The Dairy
56313 bedroom self catering cottage near the beach in Seaview.
Set in the pretty village of Seaview, moments from the seafront, this delightful home-from-home is waiting to welcome you. The village centre is a short stroll away, here you will ...
7 nights from £1329
7 nights from £1536 *
The Observatory
56934 bedroom self catering apartment near the beach in Seaview.
What a view! The most perfect seascape vistas will be found from this pretty apartment in the heart of the traditional seaside village of Seaview. This quirky home-from-home is the...
7 nights from £1536 *
7 nights from £1084 *
Tangle Cottage
56694 bedroom self catering cottage near the beach in Seaview.
Nestled at the end of Ryde Road, just a short walk from the beach and Seaview village, with off-street parking and a lovely large garden to the rear, semi-detached Tangle Cottage i...
7 nights from £1084 *
7 nights from £1254
Inglefield
56374 bedroom, dog friendly holiday cottage near the beach in St Helens.
This beautiful home close to Bembridge Harbour is a space to enjoy with family and friends. From exploring the bays and beaches to the rolling countryside and historic castles, Ing...
7 nights from £1254
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 £910
The Little Dairy Park Farm
56362 bedroom, dog friendly holiday cottage near Ryde, Isle of Wight.
This welcoming retreat is close to the pretty village of Seaview and the sandy beach at Ryde, and has the Isle of Wight Gin Distillery within walking distance. Thoughtfully present...
7 nights from £910
7 nights from £1069 *
Escape Away
56122 bedroom self catering cottage near the beach in Freshwater.
Close to the beach, a short drive from pretty Yarmouth and not far from the iconic Needles, Escape Away is the perfect luxury retreat to base yourself for a peaceful and relaxing h...
7 nights from £1069 *
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.
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