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 115 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

115 Isle of Wight cottages available for January

  • Sleeps 10 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1200

5 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of wight.


This stunning converted coach house, benefitting from a fabulous location within the grounds of the Priory Estate, is an exceptional holiday home-from-home. The Priory Coach House ...

  • Sleeps 10 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1200

  • Sleeps 10 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £1269

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


A wonderfully modern property, beautifully furnished and housed in an American-style cladded exterior, Pitt Corner is roomy, with plenty of space for the family to spread out. As w...

  • Sleeps 10 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £1269

  • Sleeps 10 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1610

5 bedroom self catering cottage near the beach in Cowes, Isle of Wight


A truly amazing, contemporary home with views directly out to sea, in the popular sailing town of Cowes. Offering exceptional quality throughout the whole home this is a superb bas...

  • Sleeps 10 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1610

  • Sleeps 12 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £1170

6 bedroom, rural self catering home with sea views in Seaview, Isle of Wight.


Bay House is an incredibly spacious and stylish Edwardian villa offering great sea views from many of its rooms. Lovingly refurbished throughout, the property is the ideal choice f...

  • Sleeps 12 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £1170

  • Sleeps 12 + 3 cots in 3 properties
  • Changeover Fri

7 nights from £1116


Mattingley Farm is made up of three beautiful cottages, each sleeping up to four guests, and is the perfect getaway for a family or friends holiday. Dairy Cottage (3912) and Orchar...

  • Sleeps 12 + 3 cots in 3 properties
  • Changeover Fri

7 nights from £1116