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 49 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. 

49 Isle of Wight cottages available for January

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

7 nights from £496

Westhill View

4882

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


With the golden sands of Shanklin beach a short walk away, this lovely holiday home sits in the heart of town, perfect for traditional days by the seaside and within easy reach of ...

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

7 nights from £496

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £567

The Stables

4537

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


The Stables is light and airy throughout with two bedrooms, a king-size double and a twin. The open plan living-room with kitchen and dining areas is warm and inviting, with doors ...

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £567

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £567

The Pigsty

4538

2 bedroom, dog friendly cottage near the beach near Brighstone, Isle of Wight.


The Pigsty is a detached barn with parking for two cars and two private seating areas alongwith a spacious communal area. There are two bedrooms, a double and a twin, each beau...

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £567

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

7 nights from £569

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 £569

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

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

7 nights from £614

1 Thatched Cottage

3508

2 bedroom thatched self catering cottage with sea views in Seaview.


If the restorative power of the sea appeals to you, 1 Thatched Cottage with its uninterrupted views is an ideal holiday home. This 19th Century property combines old world charm wi...

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

7 nights from £614

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £617

The Dairy

4536

2 bedroom, dog friendly cottage near the beach near Brighstone, Isle of Wight.


The Dairy is the largest of all four barns and is closest to The Cattle Byre. It has a spacious kitchen and dining area making it a social space for the family to gather and make p...

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £617

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

7 nights from £710

The Clock House

4559

2 bedroom self catering cottage near the beach in Yaverland, Isle of Wight.


This beautifully decorated converted former stable, in the grounds of the Old Rectory in Yaverland just outside Bembridge, is a real gem. The owner has created a stylish and indivi...

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

7 nights from £710

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

7 nights from £882

Daisy Cottage

4824

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


Daisy Cottage is a lovely cosy and welcoming mid terrace cottage nestled in the heart of Bembridge. Located in one of the most desirable areas to live in on the Isle of Wight, this...

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

7 nights from £882

  • Sleeps 5 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £616

7 Sandpipers

3568

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


7 Sandpipers is a modern townhouse, set in the heart of the popular sailing village of Seaview. Located just minutes from the seafront, with its beach, rock pools and coastal path,...

  • Sleeps 5 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £616

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £736

Limpets

4622

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


This gorgeous home, just a stone's throw from the seafront, has sea views from the sitting-room and the luxury of your very own private garden, giving it all the ingredients for a ...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £736

Our property managers are local experts who handpick perfect places to stay.

Loading more