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
1 Yarborough Cottage
37463 bedroom self catering cottage near the beach in St Helens, Isle of Wight.
1 Yarborough Cottage is a wonderfully quaint end of terrace property facing St Helens Green on the east side of the island, with far reaching views over Culver Downs. The owners ha...
Price per week £358 - £888
4 Commodores Court
35533 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
The wow factor at 4 Commodores Court is the location; perched directly opposite the beach it has stunning views of the Solent from the front, and delightful rural and lakeside view...
Price per week £374 - £930
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30% off
7 Sep 2018 - 14 Sep 2018
£534.19 £373.80
6 Tollgate Cottages
35643 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
6 Tollgate Cottages is a bright and cheery cottage set in a small, gated development near the pretty village of Seaview. Close to the beach, local shops and bars, and with Cafe Blu...
Price per week £375 - £830
10 Tollgate Cottages
35133 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
10 Tollgate Cottages is a pastel coloured, beach bungalow set in a small gated development close to the waterfront. Clean, neutral decor and its close proximity to the beach make t...
Price per week £375 - £830
24 Tollgate Cottages
35373 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight
24 Tollgate Cottages is a comfortable property just a stone's throw away from the beach, and a short walk from the local shops and dining in Seaview village. Situated on a small de...
Price per week £375 - £830
27 Tollgate Cottages
35403 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
27 Tollgate Cottages is one of a number of well presented, beachfront holiday bungalows situated in Salterns Village, a small gated development located opposite Seaview Duver and b...
Price per week £375 - £830
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!).
Heath Villa
39192 bedroom, dog friendly holiday cottage near the beach in Shanklin, Isle of Wight
This modern and bright bungalow with a south-facing garden is perfect for a family holiday and as it has a fully-enclosed rear garden, why not bring your four-legged friends? Sleep...
Price per week £384 - £850
1 Astra House
35003 bedroom, dog friendly apartment near the beach in Seaview, Isle of Wight.
1 Astra House is a comfortable, light and bright ground floor apartment set within a charming Victorian property in Seaview. Featuring an open plan layout, the dining-area, kitchen...
Price per week £398 - £895
30 Seaview Bay
35493 bedroom holiday cottage near the beach in Seaview, Isle of Wight.
30 Seaview Bay is a lovely three bedroom apartment set over two levels, offering sea views from the master bedroom balcony. Doors from the sitting-room lead to a decked area and pr...
Price per week £399 - £860
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10% off
1 Sep 2018 - 8 Sep 2018
£576.80 £519.12
Rose Villa
36493 bedroom, dog friendly holiday cottage near the beach in Yarmouth, Isle of Wight.
Rose Villa is a little gem of a home in Yarmouth with its open plan kitchen and dining-table close to the doors to the garden, capturing the light nicely on a sunny day. Continuing...
Price per week £400 - £1160
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30% off
15 Sep 2018 - 22 Sep 2018
£571.30 £399.70