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 107 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.
107 cottages available for December on the Isle of Wight
7 nights from £824
Beggars Roost
43463 bedroom self catering apartment with sea views in Seaview, Isle of Wight
This gorgeous first floor apartment in the heart of Seaview village is perfectly placed to reach everything within a few minutes' walk. The seafront is just around the corner, a po...
7 nights from £824
7 nights from £1179 *
Dolphin Cottage
43474 bedroom self catering cottage near the beach in Bembridge, Isle of Wight
Within a few minutes’ walk of the village centre and located on an unmade road leading to the sea, Dolphin Cottage is a simply stunning house ideally laid out to make space for all...
7 nights from £1179 *
7 nights from £1088 *
Sunset Cottage
43193 bedroom self catering cottage near Ventnor, Isle of Wight
Looking for the ultimate homestay for a family holiday, a celebratory escape for a couple, or simply an excuse to get together with friends, Sunset Cottage has holiday luxury cover...
7 nights from £1088 *
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10% off
26 Apr 2024 - 3 May 2024
£1117.00£1005.30
7 nights from £564
Lanthorn Cottage
42873 bedroom, dog friendly holiday cottage near the beach in St Helens, Isle of Wight
Located in a quiet side street just off the village green in St Helens, this cosy cottage offers great accommodation with a good sized garden, spacious decking and outdoor seating ...
7 nights from £564
7 nights from £1573
Buckland House
42904 bedroom self catering cottage near the beach in Seaview, Isle of Wight
Tucked out of sight yet right in the heart of Seaview, Buckland House is a stunning home, beautifully renovated by the owners and just a stone's throw from the beach and local vill...
7 nights from £1573
7 nights from £1082
Merivale
42404 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight
This lovely, light and spacious detached house located on Fairy Road in Seaview, just a short stroll from the seafront, makes a fantastic base for a wonderful holiday on the Isle o...
7 nights from £1082
Arrive at your handpicked holiday home safe in the knowledge it’s been fully inspected.
Quality inspections
We check our holiday homes to ensure that everything is up to our high standards for your holiday, from provision of our above standard minimum inventory to how fluffy the towels are, we make sure you’ll have a comfortable stay.
Hardworking teams of housekeepers will have the place spick and span, ready for your arrival, so when you get there you can just relax.
7 nights from £906
House of Logs
42254 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 and do...
7 nights from £906
7 nights from £944
Oak Tree Cottage
42123 bedroom self catering cottage with sea views in Seaview, Isle of Wight
With a stunning spacious sea facing balcony, Oak Tree Cottage is in a superb location just steps from the beach and a short walk along the seafront into Seaview Village. An outdoor...
7 nights from £944
7 nights from £525
Grace Cottage
42091 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...
7 nights from £525
7 nights from £657
1 St Josephs
41832 bedroom self catering apartment with sea views in Ventnor, Isle of Wight
With one of the best views on the Isle of Wight, 1 St Josephs is a superb ground floor apartment beautifully decorated throughout. The property has a large patio area spanning two ...
7 nights from £657
