About

For over 40 years, Classic Cottages have been the independent holiday cottage specialists. Still run and owned by the founding family, we pride ourselves on our local expertise in our areas. From family-sized homes with sea views in Ventnor to chic couples’ boltholes at the heart of Cowes, there’s something for every holiday. We love finding those interesting, secret places that you might not have heard of and sharing our best hints and tips for things to do while visiting the Isle of Wight. Our island team are our local experts, many having lived on the island for years, so please do ask for recommendations and ideas as well as any help you might need to make your holiday even better.

We cater for all types of break. Your four-legged friends are very welcome in our dog friendly properties and on many of the island’s beaches. Our baby friendly properties come 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 stay in a holiday let with a swimming pool or hot tub, or return to nature with a break at one of our chic glamping locations. 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.

Classic Cottages are VisitEngland Accredited and all properties are annually inspected.