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 145 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. 

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

145 Isle of Wight cottages available for January

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


The wow factor at 4 Commodores Court is the location; perched directly opposite the beach it has stunning views of the Solent from the front, and delightful rural and lakeside view...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £461 - £762

View
  • 30% off

    7 Sep 2018 - 14 Sep 2018

    £534.19 £373.80

3 bedroom self catering apartment near the beach in Seaview.


A ground floor apartment housed within an exclusive development, you'll feel an air of grandeur to a holiday at 3 Springfield Court with an impressive driveway just off the Seaview...

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

Price per week £470 - £906

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


A fabulous holiday home, Trevenna is contemporary in style and many thoughtful touches are provided for guests. The interior is clean and fresh, there are wooden floors throughout ...

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

Price per week £471 - £983

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

Price per week £480 - £811

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

Price per week £483 - £917

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


Welcome to Solent Peek, a lovely comfortable home in Totland on the West Coast of the Island. As the name suggests, there is sea view from the first floor master bedroom and it is ...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £495 - £954

Don’t miss out; reserve your favourite 2019 holiday cottage for just £30

3 bedroom self catering cottage in East Cowes, Isle of Wight


Turnstone is a beautifully designed, newly built town house situated overlooking the River Medina on the north coast of the island and within walking distance of Osborne House. Fro...

  • Sleeps 6 + 2 cots
  • Regret no pets
  • Changeover Sat

Price per week £495 - £842

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


With wonderful views over Bembridge Harbour and Brading Marshes, 5 Yar Quay is a charming three storey house in St Helens within walking distance of Bembridge Village. The sitting-...

  • Sleeps 6 + 2 cots
  • Dogs welcome
  • Changeover Fri

Price per week £495 - £980

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

Price per week £495 - £935

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

Price per week £500 - £900

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