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 144 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

144 cottages available for December on the Isle of Wight

  • Sleeps 9 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £860

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


This is a three-storey house right in the heart of Bembridge village, just opposite the picturesque village church and a few minutes' walk from the shops and restaurants. The prope...

  • Sleeps 9 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £860

  • Sleeps 9 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1302

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


This impressive 150 year old Farmhouse sleeps nine and is the perfect location for a fabulous family gathering of all ages. In the breathtaking location of Barton Manor Estate, adj...

  • Sleeps 9 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1302

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  • 20% off

    5 Apr 2019 - 12 Apr 2019

    £2072.45 £1657.96

  • Sleeps 10 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £732

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


Orchard House is a wonderful property for an extended family looking for a sprawling holiday home near the beach in Bembridge. The downstairs living areas are inviting - no doubt t...

  • Sleeps 10 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £732

  • Sleeps 10 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £753

5 bedroom, dog friendly holiday cottage with sea views in Wootton, Isle of Wight.


Creekside is a fabulous waterfront property that makes a wonderful choice of holiday home at any time of the year. This stunning detached house, set on the banks of Wootton Creek, ...

  • Sleeps 10 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £753

View
  • 15% off

    5 Apr 2019 - 12 Apr 2019

    £1088.06 £924.85

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

  • Sleeps 10 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £891

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


Mariners is a beautiful beachfront property offering light, spacious, contemporary family accommodation. Tastefully refurbished in recent years, this modern property is spread acro...

  • Sleeps 10 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £891

  • Sleeps 10 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £893

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


Swift Cottage is a gorgeous, comfortable Edwardian end-of-terrace property, spread over three levels with wooden flooring throughout the kitchen and dining area. The spacious dinin...

  • Sleeps 10 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £893

  • Sleeps 10 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £895

4 bedroom, rural self catering cottage near the beach in Shanklin, Isle of Wight.


Mountbatten Garden Apartment is a fabulous apartment stylishly furnished with four en suite bedrooms and comes with a private courtyard including a six person hot tub. Vibrantly de...

  • Sleeps 10 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £895

  • Sleeps 10 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £1009

5 bedroom, rural self catering cottage near the beach in Ryde, Isle of Wight.


Seacrest House is a stunning holiday home with fabulous Solent views across beautiful Appley beach and is perfect for a large family or group of friends looking for a property with...

  • Sleeps 10 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £1009

  • Sleeps 10 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1200

5 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of wight.


This stunning converted coach house, benefitting from a fabulous location within the grounds of the Priory Estate, is an exceptional holiday home-from-home. The Priory Coach House ...

  • Sleeps 10 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1200

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  • 20% off

    29 Mar 2019 - 5 Apr 2019

    £1199.80 £959.84

  • Sleeps 10 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £1269

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


A wonderfully modern property, beautifully furnished and housed in an American-style cladded exterior, Pitt Corner is roomy, with plenty of space for the family to spread out. As w...

  • Sleeps 10 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £1269

View
  • 20% off

    29 Mar 2019 - 5 Apr 2019

    £1348.48 £1078.78

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

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