January Cottages on the Isle of Wight

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 37 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. 

37 Isle of Wight cottages available for January

Tamarisk House is a 4 bedroom, dog friendly holiday cottage with sea views in Seaview, Isle of Wight.
  • Sleeps 8 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1932

Tamarisk House

5516

4 bedroom, dog friendly holiday cottage with sea views in Seaview, Isle of Wight.


If you are seeking the ultimate coastal getaway with more than a little exclusivity, look no further than this luxurious retreat in Seaview overlooking the beautiful Solent on the ...

  • Sleeps 8 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1932

Pitt Corner is a 4 bedroom self catering cottage near the beach in Bembridge, Isle of Wight.
  • Sleeps 10 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1560

Pitt Corner

3644

4 bedroom 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 a roomy retreat, with plenty of space for the family to spread...

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

7 nights from £1560

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

Harbour View is a 4 bedroom self catering cottage with sea views in Ryde, Isle of Wight.
  • Sleeps 10 + cot
  • No pets
  • Changeover Fri

7 nights from £1891

Harbour View

4731

4 bedroom self catering cottage with sea views in Ryde, Isle of Wight.


Escape to the Isle of Wight for a blissful coastal retreat at Harbour View, an impressive Grade II Listed townhouse with stunning sea views, spread over three floors, and with the ...

  • Sleeps 10 + cot
  • No pets
  • Changeover Fri

7 nights from £1891

Cara Cottage is a 5 bedroom, dog friendly holiday cottage near the beach in Bembridge, Isle of Wight.
  • Sleeps 10 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £2228

Cara Cottage

4846

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


Welcome to Cara Cottage, a stunning detached property located in the heart of Bembridge village. This eye-catching holiday home with soft pink 'Spanish inspired' exterior is beauti...

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

7 nights from £2228

Redworth is a 5 bedroom self catering home near the beach in Bembridge, Isle of Wight.
  • Sleeps 11 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £2069

Redworth

4541

5 bedroom self catering home near the beach in Bembridge, Isle of Wight.


This impressive five bedroom house is located on Ducie Avenue, a charming unmade road leading to the beach, in the village of Bembridge. Located within a few minutes walk of the lo...

  • Sleeps 11 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £2069

St Andrews is a 6 bedroom, dog friendly holiday home with hot tub near the beach in Yarmouth, Isle of Wight.
  • Sleeps 12 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £2727

St Andrews

4641

6 bedroom, dog friendly holiday home with hot tub near the beach in Yarmouth, Isle of Wight.


Wow! This spectacular converted church has the makings for the most amazing holiday, set in an elevated position with panoramic views across the surrounding countryside and a glimp...

  • Sleeps 12 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £2727

Kingston Barns

  • Sleeps 15 + 4 cots in 4 properties
  • Changeover Sat

7 nights from £2554