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 91 luxury cottages for 5 people on the Isle of Wight
New bookings can be placed for any holiday arriving on or after the 1st March 2021. COVID-19
7 nights from £435
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...
7 nights from £435
7 nights from £475
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...
7 nights from £475
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 £511
7 Sandpipers
35683 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
7 Sandpipers is a modern townhouse, set in the heart of the popular sailing village of Seaview. Located just minutes from the seafront, with its beach, rock pools and coastal path,...
7 nights from £511
7 nights from £535
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...
7 nights from £535
7 nights from £550
Elm Cottage
35973 bedroom self catering apartment with sea views in Seaview, Isle of wight.
Elm Cottage is a stylish first floor apartment brimming with character and comfort. It would suit friends travelling together, a couple or a family. From the front courtyard to ...
7 nights from £550
7 nights from £581
Westhill
41053 bedroom self catering apartment near the beach in Seaview, Isle of Wight
An incredibly stylish three bedroom ground floor apartment ideally located a few minutes' walk from the village of Seaview and the beach. A lovely large entrance hall centrally...
7 nights from £581
7 nights from £658
10 Shanklin Manor
35113 bedroom, rural self catering apartment near the beach in Shanklin, Isle of Wight.
Dating back to 1863 and converted in 2011, this superb two-storey first floor apartment is located on the outskirts of Shanklin. 10 Shanklin Manor has an elegant, monochrome interi...
7 nights from £658
7 nights from £380
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...
7 nights from £380
We’ve been raising the standards of self catering holidays since 1977.
Our family ethos
Tony and Clare Tregoning started the business back in 1977 and their dedication to quality and excellence is at the heart of everything we do. Tony is sadly no longer with us, but we still adhere to their original ethos of finding holiday homes we would like to stay in and have slowly grown the company to find the best picks of properties across the counties. Plus Clare still drops in to keep us on our toes.
As an independent, family-run company, we wouldn’t expect you to stay anywhere we wouldn’t want to stay ourselves. And we’re pretty picky. We want you to walk into your handpicked holiday home and say ‘wow’, sit back and relax.
7 nights from £398
9 Crown Court
41693 bedroom self catering cottage with sea views in Cowes, Isle of Wight.
Right in the heart of the bustling sailing town of Cowes, 9 Crown Court offers great accommodation with a stunning roof terrace boasting uninterrupted views across the rooftops to ...
7 nights from £398
7 nights from £414
Lawn End
36173 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
A hidden gem tucked away on Bluett Avenue in the peaceful Victorian village of Seaview, Lawn End makes great use of accent colours in its interior decor presenting a beautiful holi...
7 nights from £414