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
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 122 luxury cottages for 5 people on the Isle of Wight
7 nights from £383
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...
7 nights from £383
7 nights from £383
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...
7 nights from £383
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20% off
26 Apr 2019 - 3 May 2019
£482.13 £385.70
7 nights from £383
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...
7 nights from £383
7 nights from £400
Lanthorn Cottage
42873 bedroom, dog friendly holiday cottage near the beach in St Helens, Isle of Wight
Located in a quiet side street just off the village green in St Helens, this cosy cottage offers great accommodation with a good sized garden, spacious decking and outdoor seating ...
7 nights from £400
7 nights from £407
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...
7 nights from £407
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10% off
27 Apr 2019 - 4 May 2019
£498.65 £448.79
7 nights from £423
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...
7 nights from £423
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20% off
27 Apr 2019 - 4 May 2019
£528.39 £422.71
Need more time? Reserve any cottage for up to 24 hours before booking.
24hr no commitment reservations
You can reserve your holiday dates on your favourite cottage for up to 24 hours. You might need to check with other guests in your party or simply consider whether this cottage is right for your holiday, either way we’re happy to give you the time to step away and mull over your options before paying a penny.
We’ll send you a reminder to see if you want it or not so you won’t lose out. Take time to think it over, you don’t have to rush your decision. Have a cup of tea and when you’re ready, hit the button to book your holiday and start looking forward to it.
7 nights from £426
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...
7 nights from £426
7 nights from £433
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...
7 nights from £433
7 nights from £435
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...
7 nights from £435
7 nights from £438
2 Sandpipers
35253 bedroom self catering cottage near the beach in Seaview.
This modern, well-presented townhouse situated in a small development in the centre of Seaview would suit a family, a couple or several friends traveling together. It really is...
7 nights from £438
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10% off
26 Apr 2019 - 3 May 2019
£548.99 £494.09