Classic Cottages

High Street
Isle of Wight
PO34 5ES



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Special Offers

We have special offers and last minute availability on our offers page


We are a Visit England Quality Accredited Agency


  • All Year Availability
  • Baby Friendly
  • Bedding Provided (Except Cots)
  • Book Online
  • Check Availability Online
  • Coastal & Rural Locations
  • Dogs Allowed in Some Accommodation
  • Ferry Bookings Arranged
  • Free Wi-Fi
  • Fully Equipped Kitchen
  • Small & Large Properties
  • Towels Provided


Classic Cottages are the holiday cottage specialists – we’ve been handpicking the best holiday cottages since 1977. We feature over 160 properties all over the island and we think you'll love them as much as we do.

The Isle of Wight has everything you could want from a UK holiday, but on an island escape. From fisherman’s cottages perched on dramatic coastline, to hideaways in beautiful forests and seaside town houses, we’ve got the island covered. It’s only an hour’s drive from the M25 to Portsmouth so a short break is at your fingertips – hop on the ferry (we can arrange that for you) and feel a million miles away in a short space of time.

Bring the dog – we’ve many a cottage that welcomes furry friends, and bring the baby to one of our baby-friendly places to stay featuring all the paraphernalia you need without taking up too much luggage space. With last minute special offers, you can jump in the car at the drop of a hat and take a ferry on a whim when you spot a place that takes your fancy with up to 50% off.

Heritage and history abound for a spot of culture, and bring your walking boots or boat shoes to make the most of the landscape. Whatever floats your boat, you’ll find the perfect place to stay for a holiday on the Isle of Wight.

And you can be assured that by booking with Classic, we’ll dot all the i’s and cross all the t’s to make sure all you have to do is arrive, put the kettle on, feet up and relax.

The rest of our South & West world

Wondering about venturing a little further afield? Peruse our portfolio of lovely cottages covering the rest of Cornwall, Devon, Somerset, Dorset and Hampshire.

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