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 98 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. 

98 Isle of Wight cottages available for January

New bookings can be placed for any holiday arriving on or after the 1st March 2021. COVID-19

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

7 nights from £280

The Battenburg Studio

3664

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 £280

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £280

The Beatrice Studio

3666

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


Located on the first floor of Shanklin Villa, a lovely Victorian property, this small studio apartment packs a punch despite its size. Enjoying beautiful sea views from its elevate...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £280

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

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

7 nights from £356

Grace Cottage

4209

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 £356

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £387

Little Barn Retreat

4187

1 bedroom, rural self catering cottage in Newport, Isle of Wight


This absolutely gorgeous barn conversion is the perfect place for a couple's holiday, located on the Durton Farm Estate in the centre of the Island. Lovingly refurbished by the own...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £387

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

7 nights from £415

The Cadogan Apartment

3667

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 £415

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

7 nights from £415

The Worsley Apartment

3682

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 £415

  • Sleeps 3 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £495

The Cattle Byre

4535

2 bedroom, dog friendly self catering cottage near Brighstone, Isle of Wight.


The Cattle Byre has accommodation for three guests across two bedrooms, a double and a single. It has two private outdoor seating areas, the rear enclosed garden can only be access...

  • Sleeps 3 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £495

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

7 nights from £367

1 St Josephs

4183

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 £367

We are Gold accredited with the Green Tourism Business Scheme.

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

7 nights from £368

6 St Josephs

3846

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, sitting-room and master bedroom! Ideally positioned between Bonchurc...

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

7 nights from £368

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

7 nights from £369

2 Bermuda

3517

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


2 Bermuda is a lovely, neutrally decorated first floor apartment with wonderful views across the Solent, a balcony for al fresco drinks and a pretty garden. With both the beach and...

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

7 nights from £369

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