Classic Cottages – Independent Holiday Cottage specialists for over 40 years.

We’ve got 195 holiday cottages matching your search on the Isle of Wight.

Classic Cottages have been the independent holiday cottage specialists for over 40 years. Still, run and owned by the founding family, we pride ourselves on our local expertise across the South and West

From family-sized homes with sea views to chic couples’ boltholes, there’s something for every holiday on the Isle of Wight.

isle of wight self catering holiday cottages and flats

We cater for all types of break. Your four-legged friends are very welcome in our dog-friendly properties on the Island and on local beaches depending on the time of year.

isle of wight self catering holiday cottages and flats

We also have baby friendly properties with those extra things to make your holiday a little bit easier; a high chair, a stair gate, some properties even include a cot.

For a little bit of extra luxury why not stay in a holiday let with a swimming pool or hot tub. Weekend warriors might like to look at our properties for short breaks to squeeze in a holiday.

Classic Cottages is a leading holiday cottage letting agent in the South and West of England. With over 1000 properties across Cornwall, Devon, Dorset, Somerset, Hampshire and, most recently, on the Isle of Wight, we have so much choice when it comes to your holiday.

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Classic Cottages, High Street Seaview Isle of Wight PO34 5ES

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Opening Hours


9am to 8pm


9am to 8pm


9am to 8pm


9am to 8pm


9am to 8pm


9am to 5pm


Sunday 10am to 5pm 8th January - 9th April. 10am to 4pm otherwise.

We are open from 11am to 4pm on Bank Holidays. We are closed on the 1st January, 16th April and from the 24th to 26th of December