January Cottages on the Isle of Wight
Escape to the Isle of Wight for some rest and relaxation this January. With the festive blur of Christmas and New Year behind and a fresh page ahead, why not treat yourself to something special. We have 66 self-catering cottages on the Isle of Wight, all primed and ready to welcome you in from the cold this January. Find your favourite today. Read more
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.66 Isle of Wight cottages available for January
7 nights from £358
1 Harrow Cottages
46421 bedroom self catering apartment near the beach in Seaview, Isle of Wight.
This charming first floor apartment is in Nettlestone, just up the hill from Seaview and within walking distance of the beach. Surrounded by countryside there are lovely views from...
7 nights from £358
7 nights from £521 *
1 Thatched Cottage
35082 bedroom thatched, self catering cottage with sea views in Seaview, Isle of Wight.
If the restorative power of the sea appeals to you, 1 Thatched Cottage with its uninterrupted views is an ideal holiday home. This 19th Century semi-detached property combines old ...
7 nights from £521 *
7 nights from £714 *
Escape Away
56122 bedroom, dog friendly self catering cottage near the beach in Freshwater.
Close to the beach, a short drive from pretty Yarmouth and not far from the iconic Needles, Escape Away is the perfect luxury retreat to base yourself for a peaceful and relaxing h...
7 nights from £714 *
-
10% off
3 Jul 2026 - 6 Jul 2026
From £817.60 £735.84
7 nights from £714 *
Driftwood
56132 bedroom, dog friendly holiday cottage near the beach in Freshwater, Isle of Wight.
Whisk yourself away to this pretty retreat on the glorious Isle of Wight, perfect for couples and families and your four-legged companions who love to explore as much as you do. Th...
7 nights from £714 *
British Travel Awards 2025
Best company for UK holiday home rentals
7 nights from £730 *
Daisy Cottage
48242 bedroom, dog friendly holiday cottage near the beach in Bembridge, Isle of Wight.
Daisy Cottage is a lovely cosy and welcoming mid terrace cottage nestled in the heart of Bembridge. Located in one of the most desirable areas to live in on the Isle of Wight, this...
7 nights from £730 *
7 nights from £748 *
Bay View
39022 bedroom, rural holiday apartment near the beach in Freshwater, Isle of Wight
Perched above the stunning Freshwater Bay, this elegant contemporary apartment offers breathtaking views of the scenic coastline and the ultimate spot for refreshing seaside dips. ...
7 nights from £748 *
7 nights from £1186 *
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 £1186 *
7 nights from £1404 *
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 lon...
7 nights from £1404 *
7 nights from £588
The Cattle Byre
45352 bedroom, dog friendly self catering cottage near Brighstone, Isle of Wight.
Tucked away in a peaceful rural setting on the west side of the island, The Cattle Byre is a beautifully converted barn that blends rustic charm with modern comfort. Perfect for a ...
7 nights from £588
7 nights from £509
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 £509
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.
Make the most of peaceful towns, empty beaches and quiet footpaths lacing their way across the countryside this January. Explore all the Isle of Wight has to offer, breathing in the fresh, crisp air and wrapping up against the cold sea breeze. Once you've had your fill and your cheeks are sufficiently rosied, find a romantic corner of a pub and enjoy local treats as the evening draws in. At the end of the day, return to your own private haven and snuggle into a comfortable sofa as an open fire warms the room. At Classic Cottages, we want your holiday to be the best it can be and handpick all of our properties onto our books. With each one personally inspected and fully equipped, we think of everything so you don't have to. All you need to do? Sit back, relax and enjoy.
