Classic Cottages

About

Look forward to an unforgettable holiday on the Isle of Wight and choose from our collection of cottages on the Island. With more than 150 holiday cottages set along salt-kissed waterfronts and within picturesque countryside, you are sure to find just the right one for you.

A family-run company with over 45 years’ experience, at Classic Cottages we have perfected the art of holidays. Independent holiday specialists with a handpicked collection of island cottages, we promise the highest quality retreats so that you can enjoy the very best getaways. From summer escapes to winter retreats on the Isle of Wight, our selection of cottages has everything from romantic boltholes for two to large properties for family gatherings.

Whether you’re looking for somewhere quiet and cosy or close to the action, winsome and traditional or sleek and contemporary, our Isle of Wight cottage collection is as varied as it is charming. Catering for all types of breaks, you can find baby-friendly properties complete with highchairs, stair gates and cots, as well as dog-friendly cottages with great walks nearby – pawfect for sprightly pups and senior hounds alike.

For those added extras, you can refine your selection to include your favourite holiday must-haves, including reaching sea views, a bubbling hot tub, family-friendly games room, and private swimming pool. Book your favourite and look forward to spontaneous weekends and drawn-out breaks lapping up classic comforts and uncovering all there is to see and do. Wherever you choose, our beautiful collection will create truly memorable holidays.

Get in touch with our team of experts for all the latest advice. We are happy to share ideas and recommendations to help you make the most of your holiday. You can also take advantage of our exclusive ferry discounts to arrive at the Island with ease.

Classic Cottages are a leading holiday cottage letting specialist in the UK. We are VisitEngland accredited, and all properties are annually inspected. We are also a Which? Recommended Provider for UK Holiday Cottages 2021, 2022, 2023 & 2024, commended for excellent customer service, accuracy of cottage descriptions, website quality and reasonable prices.

For up-to-date availability and prices explore our collection of cottages on the Isle of Wight.