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 142 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

142 cottages available for December on the Isle of Wight

  • Sleeps 7 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £670

4 bedroom, rural self catering cottage on the outskirts of Wootton, Isle of Wight


This gorgeous stone cottage is tucked away in the most idyllic and tranquil location, surrounded by fields and woodland, this is the perfect holiday setting to truly escape from it...

  • Sleeps 7 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £670

View
  • 20% off

    21 Dec 2018 - 28 Dec 2018

    £1225.03 £980.00

  • 20% off

    28 Dec 2018 - 4 Jan 2019

    £1225.03 £980.00

  • Sleeps 7 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £795

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


Montagu is a luxurious, upper ground floor apartment forming part of a converted Victorian villa, just seconds from the beach at Shanklin. With a private patio with sea views and a...

  • Sleeps 7 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £795

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £419

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


Tradewinds is a four bedroomed yachtsman house, located within a waterside marina development of Island Harbour, just outside of Newport. There is a small courtyard to the rear of ...

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £419

  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £500

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


Beautifully decorated in neutral tones throughout, Alcantara is a well-presented, spacious property offering flexible family accommodation. This detached property has a ground floo...

  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £500

We are Gold accredited with the Green Tourism Business Scheme.

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £532

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


A smart town house, with well presented accommodation for eight set over three floors, Lucaya offers a great space with a pretty enclosed rear patio and lawn for an extended family...

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £532

View
  • 20% off

    22 Dec 2018 - 29 Dec 2018

    £981.29 £784.80

  • 20% off

    29 Dec 2018 - 5 Jan 2019

    £981.29 £784.80

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £563

4 bedroom self catering apartment near the beach in Seaview.


Crowsteps is on the first and second floor of a property tucked away in Seaview in a semi detached property. Boasting a stunning roof terrace with far reaching views over the Solen...

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £563

  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £569

3 bedroom, dog friendly holiday cottage with sea views in Brook, Isle of Wight


This pretty detached cottage can be found on a quiet lane in Brook on the south west coast. With its large, mature garden overlooking adjacent farmland, and close proximity to mile...

  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £569

  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £599

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


This bright, spacious detached house, on a quiet lane is just a 10 minute walk from the beautiful beach at Seagrove Bay. Furnished to a high standard, with four good-sized bedrooms...

  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £599

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £631

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


Mallards is a spacious, three-storey Edwardian house in Seaview village and a much-loved family home. Enjoying a great location just yards from the seafront, it's the perfect choic...

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £631

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £643

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


Middle Salterns is a pretty, end of terrace Edwardian property in the heart of Seaview, simply decorated and arranged over three floors. There are two double bedrooms and a bunk-ro...

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £643

Choose from our exclusive collection at the best prices with real time availability.

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