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 146 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

146 cottages available for December on the Isle of Wight

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

7 nights from £438

3 bedroom self catering cottage near the beach in Seaview.


This modern, well-presented townhouse situated in a small development in the centre of Seaview would suit a family, a couple or several friends traveling together. It really is...

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

7 nights from £438

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

7 nights from £444

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


Nestled in the heart of Seaview village, this lovely ground floor apartment is a stone's throw from both the coastline and village amenities, in fact it is just steps away from a f...

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

7 nights from £444

View
  • 10% off

    22 Feb 2019 - 1 Mar 2019

    £443.70 £399.33

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

7 nights from £445

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


Set in the delightful sailing village of Seaview, Blackberries is a pretty, refurbished cottage which offers a peaceful escape for families, small groups or couples alike. Comforta...

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

7 nights from £445

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

7 nights from £462

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


A hidden gem tucked away on Bluett Avenue in the peaceful Victorian village of Seaview, Lawn End makes great use of accent colours in its interior decor presenting a beautiful holi...

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

7 nights from £462

View
  • 10% off

    22 Feb 2019 - 1 Mar 2019

    £461.91 £415.72

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

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £470

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


The wow factor at 4 Commodores Court is the location; perched directly opposite the beach, it offers stunning views of The Solent to the front, and delightful rural and lakeside vi...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £470

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

7 nights from £480

3 bedroom self catering apartment near the beach in Seaview.


With a comfortable interior, an unbeatable location, manicured grounds and the beach within easy reach, 3 Springfield Court has it all. This delightful holiday home would suit a fa...

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

7 nights from £480

View
  • 20% off

    23 Feb 2019 - 2 Mar 2019

    £479.87 £383.89

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

7 nights from £480

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


Merries is a traditional beachside bungalow conveniently situated between Puckpool Park and Seaview village centre. It would suit a family wanting a convenient coastal holiday base...

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

7 nights from £480

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

7 nights from £481

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


Trevenna is a thoughtfully designed holiday home in Seaview that really delivers when it comes to space, charm and comfort. It would be ideal for a family or several couples travel...

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

7 nights from £481

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

7 nights from £490

3 bedroom self catering apartment with sea views in Seaview.


They say location is everything, and this property does not disappoint! Situated on the first floor, 2 Quay Rocks is a light-filled, modestly furnished apartment with a balcony, of...

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

7 nights from £490

View
  • 20% off

    22 Feb 2019 - 1 Mar 2019

    £489.64 £391.71

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

7 nights from £493

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


This gorgeous property is a stylishly converted coastguard cottage and really is a gem. Beautifully decorated throughout, in greys, blues and whites, it is an oasis of calm and has...

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

7 nights from £493

View
  • 20% off

    22 Feb 2019 - 1 Mar 2019

    £492.62 £394.09

Readymade beds and fluffy towels; this simple but appreciated welcome is standard with us.

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