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 62 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

62 cottages available for December on the Isle of Wight

New bookings can be placed for any holiday arriving on or after the 4th July 2020. COVID-19

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

7 nights from £362

2 bedroom self catering apartment with sea views in Seaview.


2 Bermuda is a lovely, neutrally decorated first floor apartment with wonderful views across the Solent, a balcony for al fresco drinks and a pretty garden. With both the beach and...

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

7 nights from £362

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

7 nights from £366

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


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

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

7 nights from £366

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

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

7 nights from £373

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 £373

  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £373

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 £373

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £388

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 £388

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £388

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 with...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £388

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

7 nights from £400

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


This gorgeous two bedroom terraced cottage is a few minutes from the beach, right in the heart of Seaview village, offering an ideal holiday bolthole on the picturesque Isle of Wig...

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

7 nights from £400

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

7 nights from £409

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


If you're looking for a property that's practically on the beach, then this is it! 1 Starboard House perches just opposite the beach in the cenre of Seaview village and enjoys unin...

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

7 nights from £409

We’re here to help you find your perfect place to stay 7 days a week.

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

7 nights from £410

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 £410

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £412

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


Bagwich Barn Cottage is located in a stunning setting within the grounds of the main house and with two other barns available for larger parties. A charming sun-room to the front o...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £412

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