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.
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.
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.