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. Read more
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.Choose from 76 luxury cottages for 5 people on the Isle of Wight
7 nights from £650
The Little Dairy Park Farm
56362 bedroom, dog friendly holiday cottage near Ryde, Isle of Wight.
This welcoming retreat is close to the pretty village of Seaview and the sandy beach at Ryde, and has the Isle of Wight Gin Distillery within walking distance. Thoughtfully present...
7 nights from £650
7 nights from £654
7 Sandpipers
35683 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
Perfectly situated in the heart of the popular sailing village of Seaview on the eastern side of the Isle of Wight, 7 Sandpipers is a well-equipped town house set across three floo...
7 nights from £654
Readymade beds and fluffy towels; this simple but appreciated welcome is standard with us.
Towels and readymade beds
All of our cottages provide bed linen and towels as standard, with a change of bedding included for holidays of two weeks or more. You’ll also find a fresh change of towels for each week (for in the house only, please bring your own for the beach) and tea towels a-plenty.
The beds will be readymade and waiting for you on arrival so you can simply sink into comfort and relax straight into your holiday.
7 nights from £861
10 Shanklin Manor
35113 bedroom, rural self catering apartment near the beach in Shanklin, Isle of Wight.
This superb two-storey, first floor apartment dating back to 1863 is located on the outskirts of Shanklin. 10 Shanklin Manor has an elegant, monochrome interior and the use of a la...
7 nights from £861
7 nights from £871
Limpets
46223 bedroom self catering apartment with sea views in Seaview, Isle of Wight.
This gorgeous home, just a stone's throw from the seafront, has sea views from the sitting-room and the luxury of your very own private garden, giving it all the ingredients for a ...
7 nights from £871
From £220 per night
Stargazers' Retreat
5125Luxury Yurt for 5 with sea views and outdoor bathtubs near Ventnor, Isle of Wight.
Welcome to Stargazers' Retreat, a heavenly glamping yurt nestled in rural splendour on the southerly tip of the Isle of Wight with blissful views of Reeth Bay and beyond. Situated ...
From £220 per night
7 nights from £550
Pandora Lodge
36423 bedroom self catering apartment near the beach in Seaview, Isle of Wight.
Perfectly situated in the heart of the delightful village of Seaview on the Isle of Wight, Pandora Lodge is a lovely, spacious ground floor apartment forming part of a larger prope...
7 nights from £550
7 nights from £566
East Gull Sands
35953 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
Seaview is a much sought-after and very charming village on the Isle of Wight and East Gull Sands sits in a magical position overlooking the beach, just a short stroll away from th...
7 nights from £566
7 nights from £601
25 Palmerston Road
35383 bedroom self catering cottage near the beach in Shanklin.
Welcome to 25 Palmerston Road, a delightful holiday home perfectly situated in the charming town of Shanklin and just a short stroll away from the golden sandy beach and a good sel...
7 nights from £601
Choose from our exclusive collection at the best prices with real time availability.
Exclusive cottage collections
Our calendars show live availability, so if your pick of dates are available, you can reserve them safe in the knowledge that they won’t get sold anywhere else.
It can be unpredictable using aggregator websites that collect up information from across multiple websites. Our website stands alone, so you know what to expect and what you will get, for the best price. You won’t find this collection of cottages anywhere else, so pick your perfect place to stay from our exclusive portfolio.
7 nights from £614
3 Springfield Court
35473 bedroom self catering apartment near the beach in Seaview, Isle of Wight.
With a comfortable interior, an unbeatable location, manicured grounds and the beach within easy reach, 3 Springfield Court has it all. This delightful holiday home would suit a fa...
7 nights from £614
7 nights from £619
Lawn End
36173 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
Tucked away in a quiet corner of the delightful village of Seaview, Lawn end is a cosy island retreat, tastefully furnished to offer contemporary living for families or a group of ...
7 nights from £619
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.
