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.
Choose from 83 luxury cottages for 5 people on the Isle of Wight
7 nights from £1402
Halland Rise
55004 bedroom, dog friendly holiday cottage with sea views in Seaview, Isle of Wight.
Introducing, Halland Rise, a stunning detached house sleeping eight guests, nestled in Seaview, one of the Island's most sought-after villages. With a choice of hidden coves and lo...
7 nights from £1402
7 nights from £1428
Newclose Houseboat
52004 bedroom houseboat with sea views in Bembridge, Isle of Wight
Welcome aboard Newclose Houseboat, a beautifully restored contemporary houseboat located in picturesque Bembridge harbour on the Isle of Wight, just a short stroll away from the st...
7 nights from £1428
7 nights from £1456
Solas
44594 bedroom self catering cottage with sea views in Seaview, Isle of Wight.
This superb, spacious detached house close to Seaview village has wonderful sea views from the first floor open plan sitting/dining-room and balcony. Taking full advantage of the v...
7 nights from £1456
7 nights from £1458
Leeway House
51384 bedroom, dog friendly holiday cottage near the beach in Cowes, Isle of Wight
Renowned as home to the largest sailing regatta in the world, Cowes is a pretty seaport town on the north side of the Isle of Wight, with fabulous views over the Solent and a great...
7 nights from £1458
7 nights from £1499
Fortune
43364 bedroom, dog friendly holiday houseboat with sea views in Bembridge, Isle of Wight
Step on board this simply stunning houseboat situated in the picturesque Bembridge harbour, just a short walk from Bembridge village. The beautiful bright yellow door opens to a va...
7 nights from £1499
7 nights from £1538
Dar View
54584 bedroom self catering cottage near the beach in Bembridge, Isle of Wight.
If you are looking for a stylish, spacious, yet comfortable retreat which boasts a superbly sought-after location, welcome to Dar View. An exquisite 'New England' style holiday...
7 nights from £1538
7 nights from £1573
Buckland House
42904 bedroom self catering cottage near the beach in Seaview, Isle of Wight
Tucked out of sight yet right in the heart of Seaview, Buckland House is a stunning home, beautifully renovated by the owners and just a stone's throw from the beach and local vill...
7 nights from £1573
7 nights from £1591
The Swallows
36804 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
Spread over three floors of stunning, inviting interiors, The Swallows really is a beautiful family holiday home. The gorgeous neutral decoration gives the cottage a wonderfully re...
7 nights from £1591
7 nights from £1623
Saye House
45734 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
Just a few minutes from idyllic Seagrove Bay, Saye House has been stylishly renovated to a high standard offering a wonderful place to enjoy a well-earned rest on the Isle of Wight...
7 nights from £1623
7 nights from £1684
Dolphin Cottage
43474 bedroom self catering cottage near the beach in Bembridge, Isle of Wight
Within a few minutes’ walk of the village centre and located on an unmade road leading to the sea, Dolphin Cottage is a simply stunning house ideally laid out to make space for all...
7 nights from £1684
