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 138 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

138 Isle of Wight cottages available for January

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


Number 18 is a two bedroomed chalet on the small Tollgate holiday complex on the Seaview Duver. These are ideal to rent out for larger families as you can rent next door and other ...

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

Price per week £595

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


Number 17 is located at the end of the development looking out to the shared communal grounds and Seaview Nature Reserve. There is a downstairs twin bedroom with a walk-in shower a...

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

Price per week £595

2 bedroom self catering apartment near the beach in Seaview.


A spacious, stylish, ground floor apartment in the sought-after Springfield Court complex, Apartment 4 offers guests the shared use of eight acres of mature landscaped grounds, a t...

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

Price per week £679

2 bedroom self catering apartment with sea views in Ryde.


8 Appley Sands is a spacious, purpose built, top floor apartment overlooking the Solent and the award-winning beach at Appley. With en suites to both bedrooms, and comfortable, mod...

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

Price per week £691

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

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


Westbourne Cottage is a pretty, pastel-coloured, holiday cottage, located in the picturesque Seagrove Bay. The single level accommodation (ideal for less able guests) is lightly de...

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

Price per week £692

2 bedroom, rural holiday apartment near the beach in Freshwater, Isle of Wight


This beautiful contemporary apartment is literally perched above the beach, offering stunning views of the picturesque Freshwater Bay. Extremely well appointed, the apartment offer...

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

Price per week £699 - £1100

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


With an interesting history and dating from 1852, Trevessa was once a fishing cottage and overlooks the sea. The sitting-room, dining-room and both bedrooms have beautiful sea view...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £745

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  • 25% off

    23 Nov 2018 - 30 Nov 2018

    £313.54 £235.16

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


22 Seaview Bay is an impressive two-bedroom waterfront apartment, set over two floors in the prestigious Seaview Bay development. It would suit a family with children able to navi...

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

Price per week £746

2 bedroom self catering apartment near the beach in Seaview, Isle of Wight.


10 Springfield Court is a wonderful, second floor apartment set within eight acres of beautiful communal grounds. It would ideally suit a couple or a small family. With the sea...

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

Price per week £888

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


A Victorian property set on a quiet road and yards from the beach. Oaks is a well-equipped property, decorated to a high standard and perfect for families with open plan seating an...

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £341 - £595

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

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