Isle of Wight Holidays in December

At Classic Cottages we pride ourselves on marketing only the very finest self-catering cottages on the Isle of Wight. Handpicking each one onto our portfolio, we make sure each property is personally inspected and fully equipped with everything you could need and more for a December retreat. Take a look through our portfolio and find your favourite cottage today.Read more

Can't decide whose house will bear the Christmas Day activity this year? Get everyone together in a holiday cottage this December and display the Aga-cooked turkey resplendent in the centre of the dining-table. Or try a novel way to welcome in the New Year and book a sea view apartment so you can watch fireworks bursting in the sky. Perhaps you'd like to escape for a while and revel in some peace and quiet, we have cottages both in the heart of the action and tucked away so you are sure to find something to suit you. However you'd like to spend your December getaway on the Isle of Wight, pour through our 146 available self-catering retreats and find somewhere just right for you. At Classic Cottages, we want your whole experience to be as smooth and stress-free as possible, and offer help and support every step of the way. 

Isle of Wight Ferry Booking With 200 ferries daily, our hassle free booking service makes your trip to the island plain sailing

146 cottages available for December on the Isle of Wight

  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £358

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


Quiet Corner is a modestly furnished, comfortable cottage situated in the popular village of Bembridge, less than a mile from Bembridge beach. As its name suggests it's tucked away...

  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £358

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £359

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


23 Tollgate Cottages is a comfortably furnished beach bungalow located in a small, gated waterside development on the edge of Seaview, within walking distance to the shops and cafe...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £359

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

7 nights from £359

2 bedroom self catering cottage with sea views in Ventnor, Isle of Wight


Located in the cosmopolitan town of Ventnor in a Victorian town house, Seascape is a modern two bedroom apartment with spectacular sea views along the coastline. It offers contempo...

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

7 nights from £359

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

7 nights from £361

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


5 Sandpipers is a well-equipped, modern house set within a small development in the heart of Seaview. It offers comfortable accommodation for a couple or small family. The sitt...

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

7 nights from £361

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £364

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


Originally the farm's milking parlour, this delightful cottage sleeping four is the perfect cottage to spend quality time together as a family in a stunning rural location. Located...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £364

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £364

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


Originally the farms milking parlour, Dairy Cottage is a light and airy ground floor cottage with plenty of charm throughout. With a double bedroom with pleasant views across the f...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £364

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

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

7 nights from £367

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


4 Carina is a modestly furnished, first floor apartment in a converted house which offers a great value break for families or a couple. Centrally located and just yards from the sh...

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

7 nights from £367

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

7 nights from £375

2 bedroom self catering cottage with sea views in Seaview.


North View is a wonderful holiday hideaway just on the outskirts of Seaview with sea views across the Solent from the kitchen/dining-room and first floor bedrooms. Set back from th...

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

7 nights from £375

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £377

2 bedroom, dog friendly holiday cottage in a rural setting close to Godshill, Isle of Wight


A barn conversion in a rural setting, you'll enjoy a feeling of peace from the moment you step inside this lovely retreat, with its exposed beams and rustic decor. Sitting within t...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £377

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £377

2 bedroom, dog friendly cottage in a rural setting close to Godshill, Isle of Wight.


A barn conversion, in a rural setting, with a welcoming, rustic feel to it, 1 Bagwich Barn offers an ideal base in the middle of the The Isle of Wight, from which to explore north ...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £377

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