Explore the Isle of Wight for Accommodation, Things to Do and Eating out.

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

Classic Cottages, Isle of Wight

Classic Cottages isle of WightWe’ve got over 200-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.

Our latest additions:


Seaview / Sleeps 6 + 2 cots*
(*cots are not provided bring your own travel cot) Located on the corner of Ryde Road, Westbourne is a lovely property ideally placed for Seaview Village and the beach. The village amenities are just a few minute’s stroll away and include a community store, several cafes and The Seaview Hotel. The seafront and Seaview Yacht Club are also within a five-minute walk, wander down for a morning dip in the sea and soak up the unique charm of this small Edwardian resort.

House of Logs

Totland / Sleeps 8 + cot

House of Logs is a unique and stunning property located on the west coast of the Island, just a short walk from Widdick Chine and Totland Bay. Perfect for a peaceful holiday, the house is located in a quiet road opposite the entrance to the coastal path which runs through Headon Warren, a site of Special Scientific Interest, to Alum Bay and The Needles.


Tidal Retreat

1.9 miles NE of Newport / Sleeps 6 + cot*
(*cots are not provided bring your own travel cot) This stylish three-storey townhouse is located in the exclusive development of Island Harbour, with two balconies overlooking the busy marina and providing the perfect sun-trap to enjoy a morning coffee in the stunning surroundings. The spacious open plan kitchen/dining room has sliding doors out to the balcony which also has dining seating, so whatever the weather you can enjoy mealtimes admiring the boats. There is the option to bring your own boat and a mooring is available upon arrangement for an additional cost per night.  

Oak Tree Cottage

Seaview / Sleeps 6 + 2 cots*
(*cots are not provided bring your own travel cot) With a stunning spacious sea facing balcony, Oak Tree Cottage is in a superb location just steps from the beach and a short walk along the seafront into Seaview Village. An outdoor dining table and gas barbecue make the balcony a wonderful place to relax and enjoy al fresco dining whilst admiring the view across the Solent. The current owners have reconfigured the layout so the living/dining space is on the first floor to capitalise on this idyllic location. Beautifully presented throughout, Oak Tree Cottage is a fantastic holiday destination.  

Glebe House

Bembridge / Sleeps 9 + cot*
(*cots are not provided bring your own travel cot)
This is a three-storey house right in the heart of Bembridge village, just opposite the picturesque village church and a few minutes’ walk from the shops and restaurants. The property benefits from this convenient location as well as being very private with a secluded patio area for outdoor dining and a secure lawned garden, ideal for your four-legged friend. Traditional flagstone floors and period features are to be found throughout Glebe House, creating a warm and welcoming holiday cottage to gather with family and friends.

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