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 145 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

145 cottages available for December on the Isle of Wight

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

7 nights from £682

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 £682

  • Sleeps 8 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £689

4 bedroom, dog friendly holiday cottage with sea views in St Helens, Isle of Wight


Bay View is a charming semi-detached house situated down a quiet leafy lane off the Green in the picturesque village of St Helens and aptly named due to the stunning views over St ...

  • Sleeps 8 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £689

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

7 nights from £720

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


Set within a converted Victorian villa, Eversley Apartment is a large, contemporary split level apartment. With modern furnishings, this property offers a luxury option for a coast...

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

7 nights from £720

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

7 nights from £750

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


A spacious family home, 17 Sandcove Rise is located on a quiet cul-de-sac in the pretty village of Seaview. It would suit a large family or several couples or friends traveling tog...

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

7 nights from £750

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  • 20% off

    29 Mar 2019 - 5 Apr 2019

    £750.06 £600.05

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

7 nights from £750

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


House of Logs is a unique and stunning property located on the west coast of the Island, just a short walk from Widdick Chine and Totland Bay. Perfect for a peaceful holiday, the h...

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

7 nights from £750

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

7 nights from £781

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


Spread over three floors The Swallows really is a beautiful family holiday home. The ground floor is very fresh, light and modern and has bi-folding doors leading out onto the pati...

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

7 nights from £781

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  • 20% off

    29 Mar 2019 - 5 Apr 2019

    £885.07 £708.06

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

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

7 nights from £795

3 bedroom self catering apartment with sea views in Shanklin, Isle of Wight.


Cromwell Apartment is a high end, beautifully presented, first floor apartment in a Victorian villa in Shanklin. Not your average beachfront apartment, the Cromwell comes with a de...

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

7 nights from £795

  • Sleeps 8 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £799

4 bedroom self catering cottage in Godshill, Isle of Wight


Nestled in the heart of the chocolate-box village of Godshill, this detached house has beautiful secluded gardens to the rear and everything the village can offer within a few minu...

  • Sleeps 8 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £799

  • Sleeps 8 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £841

4 bedroom, dog friendly holiday cottage with sea views in Seaview, Isle of Wight


With stunning sea views from not one but two balconies Solent View Road is a wonderful holiday destination within a few minutes' walk from Seagrove Bay. Located just on the outskir...

  • Sleeps 8 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £841

  • Sleeps 8 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £850

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


This completely refurbished cottage is nestled at the end of Ryde Road, just a short walk from the beach and Seaview village. With off-street parking and a lovely large garden to t...

  • Sleeps 8 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £850

View
  • 15% off

    22 Mar 2019 - 29 Mar 2019

    £974.98 £828.73

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