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 130 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. 

130 cottages available for December on the Isle of Wight

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £295

The Battenburg Studio

3664

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


This contemporary studio apartment enjoys a great location in Shanklin. With modern decor and open plan living, it makes a cosy retreat for a couple looking for a coastal break. ...

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £295

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £295

The Beatrice Studio

3666

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


Located on the first floor of Shanklin Villa, a lovely Victorian property, this small studio apartment packs a punch despite its size. Enjoying beautiful sea views from its elevate...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £295

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

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £300

1 Harrow Cottages

4642

1 bedroom self catering apartment near the beach in Seaview, Isle of Wight.


This charming first floor apartment is in Nettlestone, just up the hill from Seaview and within walking distance of the beach. Surrounded by countryside there are lovely views from...

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £300

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

7 nights from £380

Grace Cottage

4209

1 bedroom, dog friendly holiday cottage near the sea near Ventnor, Isle of Wight


This gorgeous barn conversion is set within the grounds of the stunning North Grounds Farm, just outside the village of Chale Green on the southern side of the Island. For the envi...

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

7 nights from £380

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £435

The Cadogan Apartment

3667

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


Sitting within a beautifully converted Victorian villa, The Cadogan Apartment offers a high standard of accommodation for a couple or lone traveller looking for a coastal break. Gu...

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £435

  • Sleeps 2
  • Regret no pets
  • Changeover Sat

7 nights from £450

19 Seaview Bay

4926

1 bedroom self catering apartment with sea views in Seaview, Isle of Wight.


Escape to the delights of 19 Seaview Bay to enjoy a slice of stunning Island Coastline, a gentle stroll around the pretty local shops, relax with an afternoon tea at Seaview Hotel,...

  • Sleeps 2
  • Regret no pets
  • Changeover Sat

7 nights from £450

  • Sleeps 2
  • Regret no pets
  • Changeover Sat

7 nights from £490

18 Seaview Bay

4996

1 bedroom self catering apartment with sea views in Seaview, Isle of Wight.


Perfectly situated in the much sought-after village of Seaview on the Isle of Wight, 18 Seaview Bay is a charming apartment found in a small development close to the village centre...

  • Sleeps 2
  • Regret no pets
  • Changeover Sat

7 nights from £490

  • Sleeps 2
  • Regret no pets
  • Changeover Sat

7 nights from £540

Oceanix

4900

1 bedroom self catering apartment with sea views in Ventnor, Isle of Wight.


A beautifully located top floor apartment in the heart of Ventnor, Oceanix provides the perfect sea-side getaway for your next Isle of Wight holiday. The property has been thoug...

  • Sleeps 2
  • Regret no pets
  • Changeover Sat

7 nights from £540

We’re here to help you find your perfect place to stay 7 days a week.

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £540

Buckland Cabin

4853

1 bedroom cabin near the beach in Seaview, Isle of Wight.


Tucked away just off the High Street in Seaview, this recently renovated and beautifully presented cabin is ideal if you are seeking a romantic hideaway for two. Step inside th...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £540

  • Sleeps 3 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £435

The Worsley Apartment

3682

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


Offering a high standard of accommodation, The Worsley Apartment is a ground floor apartment within Shanklin Villa, a beautifully converted Victorian building. With a separate kitc...

  • Sleeps 3 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £435

Loading more