Cottages on the Isle of Wight Sleeping 5 People
Open the door to a Classic cottage on the Isle of Wight and feel yourself relax. All of our cottages are perfectly kitted out, combining home comforts and modern luxuries so that you can enjoy total comfort during your stay. Choose four of your favourite people or simply indulge in some extra space, our self-catering holiday cottages for 5 people are primed and ready for you on the Isle of Wight.
Spring, summer, autumn and winter, a holiday on the Isle of Wight always delivers. Choose your favourite cottage from our selection and let the good times roll. Whether you are looking for a solo retreat for some gentle contemplation and relaxation, a family holiday or a catch up with friends, we'll find something for you amongst our collection of luxury cottages for 5 people. From spontaneous short breaks to holidays planned in advance with lots of time for excitement to build, give yourself something to look forward to.
From country to coast the Isle of Wight offers a diverse and beautiful escape. Spend your days exactly the way you want to and enjoy the holiday of a lifetime. It's good news for your four-legged friend too as many of our holiday cottages are dog-friendly.
Holiday Cottages for 5 People on the Isle of Wight
At Classic Cottages we pride ourselves on the quality of our cottages and make sure only the best are on our books. To maintain our standards, we personally inspect and handpick all of our cottages. Each one is fully equipped with a full inventory, and everything you could need for your holiday is provided. So your experience is as relaxed and easy as can be, we provide help and support every step of the way. Get in touch to find out more.
With 200 ferries daily, our hassle free booking service makes your trip to the island plain sailing
Choose from 128 luxury cottages for 5 people on the Isle of Wight
Merries
36293 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
Merries is a traditional beachside bungalow conveniently situated between Puckpool Park and Seaview village centre. It would suit a family in need an easy, convenient holiday exper...
Price per week £410 - £850
2 Sandpipers
35253 bedroom self catering cottage near the beach in Seaview.
This modern, well-presented town house is located in a small development in the centre of Seaview. A true home-from-home, 2 Sandpipers is perfect for a coastal break with the famil...
Price per week £418 - £945
Don’t miss out; reserve your favourite 2019 holiday cottage for just £30
Reserve your 2019 holiday
Our portfolio gets better year after year, with all the old favourites and some stunning new additions, so get in there quick and reserve your preferred dates for only £30.
Pick a place close to the coast for that year-round holiday vibe, or book a holiday townhouse to be close to every convenience. Escape to the country for peace and quiet or take to the moors for walks through wide open spaces, we’ve got plenty of holiday cottages for you to choose from for next year.
Reserve next year's holiday in advance to give you peace of mind and put off paying your deposit till after this summer (5th October). That way you know your preferred dates are yours for the choosing and you can get on with enjoying the rest of this year's holiday (before looking forward to the next!).
1 Harbour Strand
35053 bedroom self catering cottage near the beach in Bembridge, Isle of Wight.
1 Harbour Strand is a town house with jaunty decor, attractive furnishings and interesting prints, including some of the owners own artwork. It offers a games-room, with table-tenn...
Price per week £424 - £1220
The Limes
38133 bedroom self catering cottage near the beach in St Helens, Isle of Wight
The Limes is nestled in a corner of St Helens Green overlooking the cricket pitch, with far reaching views from the rear master bedroom over Brading Marshes. The location is peacef...
Price per week £426 - £980
25 Palmerston Road
35383 bedroom self catering cottage near the beach in Shanklin.
25 Palmerston Road is a bright, cheerfully decorated, family home and is one of our most popular properties. This property is a real find for a family looking for a home both close...
Price per week £427 - £939
Pandora Lodge
36423 bedroom self catering apartment near the beach in Seaview.
Pandora Lodge is a lovely ground floor apartment forming part of a larger Victorian property in central Seaview. With sea views from the sitting-room and large bay windows featured...
Price per week £429 - £969
Trafalgar
40573 bedroom self catering cottage near the beach in Seaview, Isle of Wight
Nestled in the heart of Seaview village this lovely ground floor apartment is a stone’s throw from the sea front and all the village amenities. Seaview is an idyllic Edwardian reso...
Price per week £435 - £1020
Blackberries
35833 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
Set in the delightful sailing village of Seaview, Blackberries is a pretty, refurbished cottage which offers a peaceful escape for families, small groups or couples alike. Comforta...
Price per week £436 - £969
Arrive at your handpicked holiday home safe in the knowledge it’s been fully inspected.
Quality inspections
We check our holiday homes to ensure that everything is up to our high standards for your holiday, from provision of our above standard minimum inventory to how fluffy the towels are, we make sure you’ll have a comfortable stay.
Hardworking teams of housekeepers will have the place spick and span, ready for your arrival, so when you get there you can just relax.
3 Harbour Strand
35433 bedroom, Pet friendly holiday cottage near the beach in Bembridge, Isle of Wight.
3 Harbour Strand is a comfortable, neutrally decorated holiday home in a small, quiet development close to Bembridge village and the harbour. It's an easy property in which to holi...
Price per week £450 - £995
East Gull Sands
35953 bedroom self catering cottage near the beach in Seaview, Isle of wight.
East Gull Sands is an attached, comfortably furnished, beachfront holiday home in Seaview. Sitting right opposite the beach this property has sea views from the upstairs double bed...
Price per week £451 - £990