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 124 luxury cottages for 5 people on the Isle of Wight
Red House
36482 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
A deceptively spacious semi-detached Victorian property, Red House has a lovely large kitchen with both a breakfast-bar and a separate dining-area from which the enclosed garden ca...
Price per week £311 - £940
Oaks
36392 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
A Victorian property set on a quiet road and yards from the beach. Oaks is a well-equipped property, decorated to a high standard and perfect for families with open plan seating an...
Price per week £334 - £740
We’re a Visit England Quality Accredited Agency for our high standards in holiday letting.
Quality Accredited Agency
Only the highest quality of accommodation is awarded Visit England accreditation. The assessment takes place over a few days and looks at all of our policies, practices and procedures, making sure we meet a five star standard for our guests.
We set our own standards above and beyond and we’re very proud of this accolade and all it represents.
1 The Saltings
35103 bedroom self catering apartment near the beach in Seaview Isle of Wight.
1 The Saltings is a lovely three bedroom, lower ground floor apartment - perfect for those with young children and buggies - and it's just a hop, skip and a jump away from the pebb...
Price per week £337 - £720
Spring Tide
36602 bedroom self catering cottage at Island Harbour, near Newport.
Spring Tide is a delightful holiday cottage situated in a small development at Island Harbour Marina on the banks of the River Medina. The marina is set in a beautiful secluded val...
Price per week £351 - £806
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20% off
20 Jul 2018 - 27 Jul 2018
£790.00 £632.00
4a Ship House
35563 bedroom self catering cottage near the beach in Seaview, Isle of Wight
4A Ship House, an attractive townhouse positioned right in the middle of Seaview, is perfect for a family looking for a coastal break. 'Ship shape' in presentation, the fantastic t...
Price per week £357 - £810
Starfish
39522 bedroom self catering apartment near the beach in Ventnor, Isle of Wight
Accessed via a set of stairs, this bright and airy first and second floor apartment offers contemporary accommodation, with large and spacious rooms packed with period features, hi...
Price per week £384 - £760
Elm Cottage
35973 bedroom self catering apartment with sea views in Seaview, Isle of wight.
Elm Cottage is a stylish, spacious first floor apartment, brimming with quirky taste and character, in the sought after village of Seaview and it enjoys sea views across the roof t...
Price per week £396 - £895
40 Trelawny Way
35553 bedroom self catering cottage near the beach in Bembridge, Isle of Wight.
The location of 40 Trelawny Way, on a quiet residential road in Bembridge, belies its extravagant interior. For those looking for a family home with an interior decorated with arti...
Price per week £405 - £1071
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.
2 Sea Whispers
39783 bedroom self catering cottage near the beach in Seaview, Isle of Wight
This charming first floor apartment is laid over two floors and situated right in the heart of Seaview village, tucked away down a quiet side street called Rope Walk, so called as ...
Price per week £405 - £950
Park Lodge Annexe
37202 bedroom, dog friendly holiday apartment near the beach in Shanklin.
Park Lodge Annexe is a beautifully presented lower ground floor apartment within walking distance to the Rylstone Gardens and the Chine. The cliff path is a minute stroll away, lea...
Price per week £407 - £837