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 30 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
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.
30 Isle of Wight cottages available for January
7 nights from £731
Barton Manor Lake Cottage
35812 bedroom, dog friendly holiday cottage near the beach in East Cowes, Isle of Wight.
Steeped in history Barton Manor is of great significance to the Isle of Wight’s heritage, situated adjacent to Osborne House and part of the original estate. The grand driveway lea...
7 nights from £731
7 nights from £896
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 £896
7 nights from £1036
Escape Away
56122 bedroom self catering cottage near the beach in Freshwater.
Close to the beach and not far from the iconic Needles, Escape Away is the perfect retreat to base yourself for a peaceful holiday. Whisk yourself away to the glorious Isle of Wigh...
7 nights from £1036
7 nights from £1036
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 there is plenty to...
7 nights from £1036
Our property managers are local experts who handpick perfect places to stay.
Local experts
We scour the coast and country to winkle out bits worth sharing with you, the best properties in lovely locations. While we’re out and about, we gather together the best things to do so that you can start planning your holiday as soon as you’ve booked.
The ‘Explore Nearby’ tab on our cottage pages show what’s nearby along with relevant articles from our holiday guides from Notes and Stories, where you’ll find hand-written experiences of outings across the South and West, from dog-friendly pubs on the Isle of Wight to free things to do in south Devon and everything in between.
7 nights from £871
Limpets
46223 bedroom self catering apartment with sea views in Seaview, Isle of Wight.
This gorgeous home, just a stone's throw from the seafront, has sea views from the sitting-room and the luxury of your very own private garden, giving it all the ingredients for a ...
7 nights from £871
7 nights from £720
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 couples travelling tog...
7 nights from £720
7 nights from £780
The Drey
51393 bedroom self catering cottage near the beach in Seaview, Isle of Wight
Located in the grand building that is Springfield Court, guests staying in this lovely holiday home can take full enjoyment of the grounds during their stay. Comfortably furnished ...
7 nights from £780
7 nights from £851
Old Bembridge House
47913 bedroom, dog friendly holiday cottage near the beach in Bembridge, Isle of Wight.
Tucked away on an unmade track just a few yards from the sea and Bembridge Yacht club, Old Bembridge House has all the makings of a perfect holiday idyll. Laid across three floors,...
7 nights from £851
7 nights from £1374
Firestone Lodge
54944 bedroom, dog friendly holiday cottage near the beach near Ryde, Isle of Wight.
Set back from the road and only a short walk from the pretty tidal estuary at Wootton Creek, Firestone Lodge sets the scene for your luxury holiday with family, friends and your mu...
7 nights from £1374
7 nights from £833
House of Logs
42254 bedroom, rural self catering cottage near the beach in Totland, Isle of Wight
House of Logs is a unique and stunning property located on the west coast of the Island, just a short walk from Widdick Chine and Totland Bay. Perfect for a peaceful holiday and do...
7 nights from £833
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.