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 151 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

151 cottages available for December on the Isle of Wight

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


Fir Cottage is an attractive and contemporary conversion of a Victorian home, located right in the heart of St Helens. The village green (England's second largest) lies a few yards...

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

Price per week £373 - £668

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

Price per week £375 - £675

Each and every one of our cottages is fully equipped with everything you’ll need on holiday.

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 w...

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

Price per week £379 - £704

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


If you are looking for a traditional cottage, look no further than Blakes Barn. Constructed from Island stone, the charm starts outside Blakes Barn with the beautiful brick work, t...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £380 - £657

3 bedroom rural self catering cottage near the beach in St Helens, Isle of Wight


Newlands is a charming detached cottage located just off the Green, in the picturesque village of St Helens. Its location is very peaceful yet within walking distance to the villag...

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

Price per week £383 - £608

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


A really lovely little bungalow, holding true to its seaside location with a nautical feel to the interior styling, Spinnakers is situated on a small private estate within walking ...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £387 - £674

3 bedroom, rural self catering cottage near the beach in Seaview, Isle of wight.


Westbourne Cottage is a pretty, pastel-coloured, holiday cottage, located in the picturesque Seagrove Bay. The single level accommodation (ideal for less able guests) is lightly de...

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

Price per week £390 - £692

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  • 20% off

    19 Oct 2018 - 26 Oct 2018

    £507.53 £406.02

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 central Seaview and enjoys uninterrupted sea...

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

Price per week £395 - £695

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

2 bedroom, dog friendly self catering cottage in 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

Price per week £395 - £700

2 bedroom, dog friendly holiday apartment with sea views in Ventnor, Isle of Wight.


Gilmerton is a charming and spacious apartment, beautifully decorated, and located on the outskirts of the vibrant town of Ventnor. The house is built into the hill so this first f...

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

Price per week £401 - £704

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