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 123 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. 

Isle of Wight Ferry Booking With 200 ferries daily, our hassle free booking service makes your trip to the island plain sailing

123 Isle of Wight cottages available for January

  • Sleeps 6 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £663

3 bedroom, dog friendly holiday cottage near the beach in St Helens, Isle of Wight


A simply gorgeous three bedroom property just off St Helens' green on the eastern side of the Isle of Wight, The Haven is just a short walk from the coast and a ten minute stroll t...

  • Sleeps 6 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £663

  • Sleeps 6
  • Regret no pets
  • Changeover Fri

7 nights from £925

3 bedroom self catering houseboat with sea views in Bembridge, Isle of Wight


Welcome aboard this luxury two-storey houseboat in Bembridge harbour with two rear balconies and a private pontoon, you can kayak right up to your back door just in time for lunch....

  • Sleeps 6
  • Regret no pets
  • Changeover Fri

7 nights from £925

  • Sleeps 7 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £445

3 bedroom, dog friendly holiday cottage near the beach in Totland, Isle of Wight


If you long for picturesque walks in the daytime and quiet nights under starry skies, then Ashmead Cottage is your holiday ideal. This lovely property would suit a family or even t...

  • Sleeps 7 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £445

  • Sleeps 7 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £546

4 bedroom self catering cottage near the beach in Seaview, Isle of Wight.


This light, beautifully presented holiday home offers quality accommodation with wooden floors, whitewashed walls and interesting prints and furnishings lending splashes of colour ...

  • Sleeps 7 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £546

  • Sleeps 7 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £795

3 bedroom, rural self catering cottage near the beach in Shanklin, Isle of Wight.


Montagu is a luxurious, upper ground floor apartment forming part of a converted Victorian villa, just seconds from the beach at Shanklin. With a private patio with sea views and a...

  • Sleeps 7 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £795

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £427

4 bedroom self catering cottage near the beach in Binfield, Isle of Wight.


Tradewinds is a four bedroomed yachtsman house, located within a waterside marina development of Island Harbour, just outside of Newport. There is a small courtyard to the rear of ...

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £427

Need more time? Reserve any cottage for up to 24 hours before booking.

  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £510

3 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.


Beautifully decorated in neutral tones throughout, Alcantara is a well-presented, spacious property offering flexible family accommodation in the heart of Seaview. This detache...

  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £510

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £559

4 bedroom self catering cottage near the beach in Ryde, Isle of Wight.


A smart town house, with well presented accommodation for eight set over three floors, Lucaya offers a great space with a pretty enclosed rear patio and lawn for an extended family...

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £559

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £575

4 bedroom self catering apartment near the beach in Seaview.


Crowsteps is on the first and second floor of a property tucked away in Seaview in a semi detached property. Boasting a stunning roof terrace with far reaching views over the Solen...

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £575

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £580

3 bedroom, Rural holiday cottage with sea views in Brook, Isle of Wight


This pretty detached cottage can be found on a quiet lane in Brook on the south west coast. With its large, mature garden overlooking adjacent farmland, and close proximity to mile...

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £580

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