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 118 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

118 Isle of Wight cottages available for January

We are no longer accepting new bookings for holidays arriving before the 4th July 2020. COVID-19

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £260

1 bedroom self catering apartment near the beach in Shanklin, Isle of Wight.


This contemporary studio apartment enjoys a great location in Shanklin. With modern decor and open plan living, it makes a cosy retreat for a couple looking for a coastal break. ...

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £260

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £287

1 bedroom self catering apartment near the beach in Bembridge, Isle of Wight.


This charming one bedroom apartment forms part of a country house, set around a shared Spanish-style courtyard, just outside the bustling village of Bembridge. You can enjoy th...

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £287

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

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £336

1 bedroom self-catering cottage near Ventnor, Isle of Wight


Located in a rural village setting, Berryl Mead View is a delightful home from home cottage with plenty of space. It is well-equipped throughout and has an extremely comfortable li...

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £336

  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £350

1 bedroom, dog friendly holiday cottage near the sea near Ventnor, Isle of Wight


This gorgeous barn conversion is set within the grounds of the stunning North Grounds Farm, just outside the village of Chale Green on the southern side of the Island. For the envi...

  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £350

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £385

1 bedroom self catering apartment near the beach in Shanklin, Isle of Wight.


Sitting within a beautifully converted Victorian villa, The Cadogan Apartment offers a high standard of accommodation for a couple or lone traveller looking for a coastal break. Gu...

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £385

  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £478

2 bedroom, dog friendly holiday cottage near the beach in Bembridge, Isle of Wight


Beginning its life as accommodation for troops during the First World War, The Blue Beach House has undergone many transformations in its time until its present day status as a cha...

  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £478

  • Sleeps 3 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £385

1 bedroom self catering apartment near the beach in Shanklin, Isle of Wight.


Offering a high standard of accommodation, The Worsley Apartment is a ground floor apartment within Shanklin Villa, a beautifully converted Victorian building. With a separate kitc...

  • Sleeps 3 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £385

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £357

2 bedroom self catering apartment near the beach in Ryde.


6 Pier View Court, perfectly located right on the seafront at Ryde, is a modern, well presented second floor apartment, tastefully decorated and furnished to a high standard. Relax...

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £357

Each and every one of our cottages is fully equipped with everything you’ll need on holiday.

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £360

2 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 ...

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £360

  • Sleeps 4 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £360

2 bedroom self catering apartment with sea views in Ventnor, Isle of Wight


6 St Josephs is a top floor apartment with stunning panoramic sea views, which you can admire from the balcony, living-room and master bedroom! Ideally positioned between Bonchurch...

  • Sleeps 4 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £360

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