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 6 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £481

3 bedroom self catering cottage near the beach in Seaview, Isle of Wight.


Trevenna is a thoughtfully designed holiday home in Seaview that really delivers when it comes to space, charm and comfort. It would be ideal for a family or several couples travel...

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £481

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £490

3 bedroom self catering apartment with sea views in Seaview.


They say location is everything, and this property does not disappoint! Situated on the first floor, 2 Quay Rocks is a light-filled, modestly furnished apartment with a balcony, of...

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £490

View
  • 20% off

    15 Feb 2019 - 22 Feb 2019

    £489.64 £391.71

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

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £493

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


This gorgeous property is a stylishly converted coastguard cottage and really is a gem. Beautifully decorated throughout, in greys, blues and whites, it is an oasis of calm and has...

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £493

View
  • 20% off

    15 Feb 2019 - 22 Feb 2019

    £492.62 £394.09

  • Sleeps 6
  • Regret no pets
  • Changeover Sat

7 nights from £500

3 bedroom self catering cottage with sea views in Cowes, Isle of Wight.


Right in the heart of the bustling sailing town of Cowes, 9 Crown Court offers great accommodation with a stunning roof terrace boasting uninterrupted views across the rooftops to ...

  • Sleeps 6
  • Regret no pets
  • Changeover Sat

7 nights from £500

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £505

3 bedroom self catering cottage near the beach in Bembridge, Isle of Wight


This charming cottage is tucked away down an unmade road just off Bembridge Harbour, within walking distance of Bembridge village centre. The front and rear gardens of Old Railway ...

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £505

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £531

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


Rose Villa is a beautifully appointed home in the heart of the village of Yarmouth. It would ideally suit a family or a group of friends traveling together. This spacious prope...

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £531

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £555

3 bedroom, dog friendly cottage near the beach in East Cowes, Isle of Wight.


This truly lovely holiday home, with a wood-burner, is a great choice whatever the season. 1 Barton Lodge is a beautiful property which has been lovingly restored with your comfort...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £555

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £565

3 bedroom, rural self catering cottage near the beach in Merstone, Isle of Wight.


The Barn, a linked country cottage with a rustic interior and some exposed wooden beams, is located on the outskirts of Merstone and just minutes from the quaint village of Godshil...

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £565

Our guests rate us 4.8/5 on Feefo, the independent review site.

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £592

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


A seaside sanctuary, Shore House is a three-storey beautifully decorated house, with its own private heated swimming pool. Making the most of the far reaching views over the Solent...

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £592

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £595

3 bedroom self catering cottage near the beach in St Helens, Isle of Wight


Primrose Cottage is a fully modernised and beautifully furnished Victorian three bedroom cottage situated just off the green in St Helens and offering everything you might need for...

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £595

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