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 138 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.
With 200 ferries daily, our hassle free booking service makes your trip to the island plain sailing
138 Isle of Wight cottages available for January
Gilmerton
36052 bedroom, dog friendly holiday apartment with sea views in Ventnor, Isle of Wight.
Gilmerton is a charming and spacious apartment, beautifully decorated, and located on the outskirts of the vibrant town of Ventnor. The house is built into the hill so this first f...
Price per week £410 - £704
Vida Floating Home
36902 bedroom, dog friendly houseboat on the sea in Bembridge Harbour, Isle of Wight.
For a holiday with a difference this is it! Situated on a private pontoon in Bembridge Harbour, you will have fond memories of your time on this unique floating home for years to c...
Price per week £420 - £730
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1 St Josephs
41832 bedroom self catering apartment with sea views in Ventnor, Isle of Wight
With one of the best views on the Isle of Wight, 1 St Josephs is a superb ground floor apartment beautifully decorated throughout. The property has a large patio area spanning two ...
Price per week £425 - £725
Ledge View
37643 bedroom, dog friendly cottage near the beach in Bembridge.
Ledge View is a beautifully renovated semi-detached home just steps away from Forelands beach, lined with quirky beach huts, stretches of white sand, rock pools and an acclaimed ca...
Price per week £429 - £1209 *
* Includes 35% off for parties up to 4 + cot between 5 Jan and 9 Feb 2019. Only two bedrooms are available at the discounted rate, please confirm which bedrooms you wish to use on booking.
2 St Josephs
35302 bedroom self catering apartment with sea views in Ventnor.
With sea views from the terrace, and fresh, modern décor throughout, 2 St Josephs is a holiday maker's home-from-home. It's the perfect get-away for a small family, a couple or two...
Price per week £448 - £754
50 Solent View
41443 bedroom self catering cottage near the beach in Seaview, Isle of Wight
This is a wonderfully secluded property with a charming garden and spacious balcony, all within a few minutes from the idyllic Seagrove Bay in Seaview. There are several steps up t...
Price per week £450 - £700
2 Springfield Court
35292 bedroom self catering apartment near the beach in Seaview.
2 Springfield Court is an exclusive, ground floor apartment set within a gated development. Boasting eight acres of shared grounds, guests can enjoy use of the extensive grounds, h...
Price per week £458 - £844
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...
Price per week £525 - £897
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.
4 Carina
35522 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
4 Carina is a modestly furnished, first floor apartment in a converted house which offers a great value break for families or a couple. Centrally located and just yards from the sh...
Price per week £553
18 Tollgate Cottage
37582 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight
Number 18 is a two bedroomed chalet on the small Tollgate holiday complex on the Seaview Duver. These are ideal to rent out for larger families as you can rent next door and other ...
Price per week £595