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 119 luxury cottages for 5 people on the Isle of Wight
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
5 Apr 2019 - 12 Apr 2019
£626.00 £563.40
7 nights from £444
Trafalgar
40573 bedroom self catering cottage near the beach in Seaview, Isle of Wight
Nestled in the heart of Seaview village, this lovely ground floor apartment is a stone's throw from both the coastline and village amenities, in fact it is just steps away from a f...
7 nights from £444
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10% off
29 Mar 2019 - 5 Apr 2019
£510.00 £459.00
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 £445
Blackberries
35833 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
Set in the delightful sailing village of Seaview, Blackberries is a pretty, refurbished cottage which offers a peaceful escape for families, small groups or couples alike. Comforta...
7 nights from £445
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10% off
30 Mar 2019 - 6 Apr 2019
£502.81 £452.53
7 nights from £462
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 £462
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10% off
29 Mar 2019 - 5 Apr 2019
£530.61 £477.55
7 nights from £470
4 Commodores Court
35533 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
The wow factor at 4 Commodores Court is the location; perched directly opposite the beach, it offers stunning views of The Solent to the front, and delightful rural and lakeside vi...
7 nights from £470
7 nights from £479
6 Coastguard Cottages
35583 bedroom, dog friendly holiday cottage near the beach in Brook, Isle of Wight.
Formerly the officer's quarters of the coastguard station, 6 Coastguard Cottages has been beautifully decorated and offers a wonderful holiday home in Brook. This period property h...
7 nights from £479
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10% off
11 May 2019 - 18 May 2019
£608.95 £548.10
7 nights from £480
3 Springfield Court
35473 bedroom self catering apartment near the beach in Seaview.
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 £480
7 nights from £480
Merries
36293 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
Merries is a traditional beachside bungalow conveniently situated between Puckpool Park and Seaview village centre. It would suit a family wanting a convenient coastal holiday base...
7 nights from £480
Each and every one of our cottages is fully equipped with everything you’ll need on holiday.
Fully equipped cottages
All of our cottages have a standard list of equipment that goes above and beyond. As well as fluffy towels and readymade beds, our bare minimum includes everything you’ll need and more, from plenty of teaspoons to added extras such as gravy boats so no matter where you stay, you’ll be able to make your favourite home-cooked dishes.
Each inventory is regularly checked and counted so you won’t be stuck without a ladle and can leave your hairdryer at home, plus you’ll find a starter set of toiletries and cleaning products so you can get on with your holiday.
7 nights from £480
The Barn
36633 bedroom, rural self catering cottage near the beach in Merstone, Isle of Wight.
The Barn, a linked country cottage with a rustic interior and some exposed wooden beams, is located on the outskirts of Merstone and just minutes from the quaint village of Godshil...
7 nights from £480
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15% off
30 Mar 2019 - 6 Apr 2019
£565.02 £480.27
7 nights from £481
Trevenna
36863 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
Trevenna is a thoughtfully designed holiday home in Seaview that really delivers when it comes to space, charm and comfort. It would be ideal for a family or several couples travel...
7 nights from £481