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 112 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.
112 cottages available for December on the Isle of Wight
7 nights from £1458
Leeway House
51384 bedroom, dog friendly holiday cottage near the beach in Cowes, Isle of Wight
Renowned as home to the largest sailing regatta in the world, Cowes is a pretty seaport town on the north side of the Isle of Wight, with fabulous views over the Solent and a great...
7 nights from £1458
7 nights from £795
The Drey
51393 bedroom self catering cottage near the beach in Seaview, Isle of Wight
Located in the grand building that is Springfield Court, guests staying in this lovely holiday home can take full enjoyment of the grounds during their stay. Comfortably furnished ...
7 nights from £795
From £149 per night *
Stargazers' Retreat
5125Luxury Yurt for 5 near the beach near Ventnor, Isle of Wight.
Welcome to Stargazers' Retreat, a heavenly glamping yurt nestled in rural splendour on the southerly tip of the Isle of Wight with blissful views of Reeth Bay and beyond. Situated ...
From £149 per night *
7 nights from £676 *
Sheldonia
51093 bedroom self catering cottage with sea views in Ventnor, Isle of Wight.
Welcome to Sheldonia, a hidden gem in the delightful seaside town of Ventnor and within touching distance of Steephill Cove - one of the Island's prettiest beaches, featured in The...
7 nights from £676 *
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25% off
10 Aug 2024 - 17 Aug 2024
£1615.00 £1211.25
7 nights from £1685
Beachside
51003 bedroom self catering cottage with sea views in Ventnor, Isle of Wight.
Welcome to your Island idyll, beautifully styled to offer contemporary seaside living at its best and perfectly situated on the beachfront in the heart of the much sought-after tra...
7 nights from £1685
7 nights from £1018
Underwood Cabin
49953 bedroom, dog friendly self catering cottage near Yarmouth, Isle of Wight.
Nestled in the beautiful grounds of St Hubert's Lodge and surrounded by tranquil woodlands and green pastures, Underwood Cabin is a delightful island retreat, perfectly situated be...
7 nights from £1018
Choose from our exclusive collection at the best prices with real time availability.
Exclusive cottage collections
Our calendars show live availability, so if your pick of dates are available, you can reserve them safe in the knowledge that they won’t get sold anywhere else.
It can be unpredictable using aggregator websites that collect up information from across multiple websites. Our website stands alone, so you know what to expect and what you will get, for the best price. You won’t find this collection of cottages anywhere else, so pick your perfect place to stay from our exclusive portfolio.
7 nights from £480
18 Seaview Bay
49961 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, sunny apartment found in a small development close to the village...
7 nights from £480
7 nights from £987
Sea Lights
49672 bedroom coastal holiday home with sea views in Cowes, Isle of Wight.
Situated close to the beating heart of world-famous Cowes, lies the pretty coastal village of Gurnard, where you will find this handsome coastal ground floor pet friendly apartment...
7 nights from £987
7 nights from £567
Oceanix
49001 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 seaside getaway for your next Isle of Wight holiday. The property has been though...
7 nights from £567
7 nights from £550
19 Seaview Bay
49261 bedroom self catering cottage near the beach 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 ...
7 nights from £550
