Luxury Cottages for 4 People on the Isle of Wight
Enjoy a luxury island retreat and book a holiday cottage for up to four people on the Isle of Wight. There's room for you and three of your nearest and dearest, and many of our cottages are dog-friendly too. Browse through our selection of 101 available self-catering cottages and take a step closer to the holiday of a lifetime. Read more
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.We have 101 self catering cottages for 4 on the Isle of Wight
7 nights from £461 booking fees included
The Beach Retreat
36652 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
Perfectly situated just a stone's throw away from Seaview beach, where you will discover beautiful views across the Solent, The Beach Retreat is located close to the village centre...
7 nights from £461
7 nights from £466 booking fees included
Sugar Beach
51022 bedroom dog friendly self catering cottage near the beach in Seaview, Isle of Wight
Seaview is a much sought-after charming village on the east of the Isle of Wight, and Sugar Beach is perfectly situated just a stone's throw from the beach and a short stroll away ...
7 nights from £466
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 £466 booking fees included
Cockleshells
38152 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight
Seaview is a wonderful base for an Isle of Wight holiday and Cockleshells sits in the perfect location, just a short stroll from the glorious beach and centre of the village. Situa...
7 nights from £466
7 nights from £487 booking fees included
Hove To
37672 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight
The Isle of Wight is a fabulous place for a year-round holiday and Hove To is in a great location in the sought after village of Seaview on the eastern side of the Island. With vie...
7 nights from £487
British Travel Awards 2025
Best company for UK holiday home rentals
7 nights from £490 booking fees included
Berry Cabin
52862 bedroom, dog friendly, bolthole in Seaview, Isle of Wight.
What a little cutie! Berry Cabin is a delightful bolthole for four guests and one well behaved doggy looking for some summer fun! Surrounded by Hersey nature reserve and countrysid...
7 nights from £490
7 nights from £513 booking fees included
Bay Cottage
61502 bedroom self catering cottage near the beach in Cowes.
Tucked away in the charming village of Gurnard on the northwest coast of the Isle of Wight, this cosy two bedroom cottage offers a relaxed coastal lifestyle, complete with a pretty...
7 nights from £513
7 nights from £523 booking fees included
Faithfull Cottage
36002 bedroom, dog friendly holiday cottage near the beach in St Helens, Isle of Wight.
Faithfull Cottage is a welcoming retreat situated within two miles distance of St Helens village on the Isle of Wight, as well as a gorgeous beach, RSPB Nature Reserve and the vill...
7 nights from £523
7 nights from £572 booking fees included
2 Bermuda
35172 bedroom self catering apartment with sea views in Seaview, Isle of Wight.
Welcome to 2 Bermuda, a rather lovely first floor apartment nestled in the charming village of Seaview, with wonderful views stretching across the Solent - ideal for an unforgettab...
7 nights from £572
7 nights from £573 * booking fees included
Lucaster
43073 bedroom, dog friendly holiday cottage near the beach in Fishbourne, Isle of Wight
This gorgeous, cosy, former coastguard's cottage sits in a peaceful setting in Fishbourne and is just a few yards from the sea and the welcoming local pub. Lucaster is perfectly pl...
7 nights from £573 *
7 nights from £584 * booking fees included
48 Solent View
58283 bedroom self catering cottage with sea views in Seaview.
Just a short wander from the golden sands of Seagrove Bay and the quaint charm of Seaview village, this stylish holiday haven offers modern home comforts in an unbeatable location ...
7 nights from £584 *
British Travel Awards 2025
Best company for UK holiday home rentals
Spending time with our friends and family is really important, but it's not always that easy to get together and catch up. Holiday cottages provide great neutral ground in beautiful settings, away from the distractions of everyday life. Spend time together in a luxury self catering cottage sleeping up to 4 people and rediscover yourselves.
Self Catering Cottages on the Isle of Wight for Four People
At Classic Cottages we pride ourselves on marketing only the finest holiday cottages on the Isle of Wight. Each one of our self catering cottages is personally inspected and fully equipped to ensure your total comfort. Take your time looking through our collection of 101 available holiday cottages and find the perfect one waiting for you.
