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Isle of Wight Holiday Cottages can be found across the Island, in both coastal and inland locations, and offer great flexibility alongside many of the home comforts that we all know and love.
For many the perfect Isle of Wight break represents a traditional holiday cottage in a picturesque location, and for those searching for this ideal there is plenty to offer!
Classic Cottages offers quality cottages across the Island in rural and coastal locations. From simple to sumptuous there are properties to suit all tastes, and budgets!
One of the reasons holiday cottages on the Isle of Wight offer a perfect escape is that many are located in secluded, rural areas, often as part of working / former farms.
Some of these cottages are charming conversions of historic and former working buildings, allowing you to "step back in time" during your holiday.
There are also cottages contained within some of the holiday parks, giving you access to a range of great shared facilities - like eateries, sports facilities, swimming pools, children's areas and entertainment.
To find your perfect cottage you can browse accommodation using the left hand search tool, where you can filter results by availability and the area you wish to stay in.
If you prefer you can use “advanced search” which will allow you to search for specific facilities.
Some self-catering cottages can be booked with ferry included, so enter the words “ferry inclusive” into the keywords box at the bottom of the search bar to find them.
Below is a list of Isle of Wight holiday cottages if you are looking to browse.
Number of results: 71
, currently showing 1 to 20.
SEAVIEW
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.
BROOK
AwardClose to the beach, surrounded by National Trust land & in the middle of the AONB, Brook House is a beautiful and peaceful location for a lovely self-catering holiday cottage.
BROOK
Self CateringClose to the beach, surrounded by National Trust land & in the middle of the AONB, Brook House is a beautiful and peaceful location for a lovely self-catering holiday cottage.
St Lawrence, VENTNOR
Self CateringSet in the Undercliff area of Outstanding Natural Beauty, Woodcliffe stands in peaceful secluded terraced gardens. The house, cottage and modern apartments face south across the Undercliff offering superb views of the English Channel.
WHITWELL
Self Catering AwardNettlecombe Farm is nestled in the heart of the rolling South Wight countryside offering luxurious self-catering accommodation in 9 high quality self-contained properties that sleep between 3-10 situated in the main farmhouse.
FRESHWATER
Comfortable self-catering holiday accommodation for 2-3 adults. Available for short or long breaks all year round.
BROOK
AwardClose to the beach, surrounded by National Trust land & in the middle of the AONB, Brook House is a beautiful and peaceful location for a lovely self-catering holiday cottage.
COLWELL BAY
The Bay Colwell is situated on the beautiful west coast of the Isle of Wight and just a short stroll from the wonderful Colwell Bay beach.
YARMOUTH
Impressive Self Catering Manor
Big enough to sleep the largest of families but equally cosy and welcoming; Tapnell Manor has recently undergone a major refurbishment bringing the interior into the 21st century while maintaining the rustic...
3– 5 Charming cottages in delightful rural surroundings and close to the sea. Beautiful views and lovely gardens. Carefully selected individual cottages situated throughout the Isle of Wight, accommodating from 2 to 12 people.
YARMOUTH
The Dairyman's Cottage is a beautiful holiday cottage in the Heart of Tapnell Farm which boasts spectacular views over the west of the Isle of Wight towards Tennyson downs and Freshwater Bay.
FRESHWATER BAY
Our holiday cottage is at the heart of the conservation area on the Tennyson Mile between the beach and Farringford at Freshwater Bay. The one-bedroom vacation rental has a sunny private garden. It is very quiet and perfect for two.
TOTLAND BAY
Self Catering AwardRomany Cottage, sleeping 6 in 3 rooms (2 doubles and a twin) is a beautiful cottage, quiet and an excellent base to explore the Island whether by car, walking or by bus. It offers an upstairs bathroom and two w.c.s, gas central heating, open fire...
BEMBRIDGE
Harrison Bristow Holiday Lettings is a holiday letting company offering a wide range of cottages and houses on the Isle of Wight, coastal and rural and many of our cottages accept pets.
SHORWELL
Brookside Cottage has a delightful little brook running alongside the garden. Whilst now modernised, the property dates back to 1700.
BRIGHSTONE
The Stable was once a Victorian stable that has now been converted into a beautiful detached holiday cottage to accommodate ideally 2 people. Within the picturesque village of Brighstone, near to forest, down, and within a mile of the sea.
YARMOUTH
Tanners is located in quiet Port La Salle around 1 mile (5 minute drive/20 minute walk, mostly along the Solent esplanade) from the centre of Yarmouth.
Yafford, SHORWELL
Pond Cottage and Willow Cottage are located in the peaceful hamlet of Yafford, Isle of Wight, close to the Island’s beautiful southern coastline and beaches.
RYDE
Tea Tree Cottage is a beautiful, luxury, Grade II listed, Victorian villa which sleeps 8.
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