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.

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 152 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

152 cottages available for December on the Isle of Wight

3 bedroom, rural self catering cottage in Newport, Isle of Wight


This property is a truly idyllic cottage situated in the grounds of a farm, with stunning countryside views and a covered hot tub. This is what you would describe as holiday heaven...

  • Sleeps 6 + 2 cots
  • Regret no pets
  • Changeover Sat

Price per week £600 - £1100

3 bedroom self catering cottage near the beach in Seaview.


In a quiet position within a secluded courtyard in Seaview, Raleigh Cottage is complete with a cosy wood-burning stove for the cooler months, lovely decking for outside dining and ...

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Fri

Price per week £625 - £1205

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  • 15% off

    21 Sep 2018 - 28 Sep 2018

    £670.04 £569.53

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


Right in the heart of Seaview village, this semi-detached property has been completely renovated, with a Skandi theme, to offer a wonderful place to stay on the Isle of Wight. With...

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Fri

Price per week £630 - £1050

3 bedroom, dog friendly cottage near the beach in Bembridge.


Ledge View is a beautifully renovated semi-detached home just steps away from Forelands beach, lined with quirky beach huts, stretches of white sand, rock pools and an acclaimed ca...

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

Price per week £648 - £1209

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  • 10% off

    22 Sep 2018 - 29 Sep 2018

    £745.22 £670.69

Don’t miss out; reserve your favourite 2019 holiday cottage for just £30

3 bedroom, dog friendly holiday cottage near the beach in St Helens, Isle of Wight


A simply gorgeous three bedroom property just off St Helens' green on the eastern side of the Isle of Wight, The Haven is just a short walk from the coast and a ten minute stroll t...

  • Sleeps 6 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

Price per week £650 - £1350

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


This lovely and well-presented detached house is just moments away from the beautiful golden beaches of Ryde and mainland transport links, creating a perfect location for a base fo...

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Sat

Price per week £655 - £1100

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


Ashmead Cottage has been thoughtfully decorated throughout offering three lovely bedrooms and two modern bathrooms. The kitchen opens out onto a charming private decked-area with o...

  • Sleeps 7 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

Price per week £437 - £863

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


This light, beautifully presented holiday home offers quality accommodation with wooden floors, whitewashed walls and interesting prints and furnishings lending splashes of colour ...

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

Price per week £535 - £1028

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

Price per week £670 - £1225

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

Price per week £795 - £1395

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  • 20% off

    21 Sep 2018 - 28 Sep 2018

    £995.00 £796.00

Arrive at your handpicked holiday home safe in the knowledge it’s been fully inspected.

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