We've found 87 self catering cottages for Christmas and New Year on the Isle of Wight.
7 nights from £630
Spinnakers
36592 bedroom, dog friendly holiday cottage near the beach in Yarmouth, Isle of Wight.
Situated in a peaceful, private estate just a short stroll from the charming seaside town of Yarmouth, Spinnakers is a cosy, single-storey semi-detached holiday home with well-kept...
7 nights from £630
7 nights from £643
1 Starboard House
35072 bedroom, rural self catering cottage near the beach in Seaview, Isle of Wight.
If you're looking for a property that's practically on the beach, then this is it! 1 Starboard House perches just opposite the beach in the centre of Seaview village and enjoys uni...
7 nights from £643
Our property managers are local experts who handpick perfect places to stay.
Local experts
We scour the coast and country to winkle out bits worth sharing with you, the best properties in lovely locations. While we’re out and about, we gather together the best things to do so that you can start planning your holiday as soon as you’ve booked.
The ‘Explore Nearby’ tab on our cottage pages show what’s nearby along with relevant articles from our holiday guides from Notes and Stories, where you’ll find hand-written experiences of outings across the South and West, from dog-friendly pubs on the Isle of Wight to free things to do in south Devon and everything in between.
7 nights from £646
Winkle Cottage
43952 bedroom self catering cottage near the beach in Cowes, Isle of Wight.
This gorgeous terraced cottage, situated in the Conservation Area of the old town of Cowes, is just a few minutes' walk from the centre of town, offering the perfect family holiday...
7 nights from £646
-
20% off
26 Jun 2026 - 3 Jul 2026
From £961.00 £768.80
7 nights from £657
2 St Josephs
35302 bedroom self catering apartment with sea views in Ventnor, Isle of Wight.
With sea views from the terrace and fresh, modern decor throughout, 2 St Josephs is a holiday maker's home-from-home. It is the perfect getaway for a small family, a couple or two ...
7 nights from £657
7 nights from £685
Pebbles
43982 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
Seaview is a wonderful place for an Isle of Wight holiday and Pebbles is perfectly situated in the heart of the village on a quiet residential street just a stone's throw away from...
7 nights from £685
7 nights from £688 *
1 Thatched Cottage
35082 bedroom thatched, self catering cottage with sea views in Seaview, Isle of Wight.
If the restorative power of the sea appeals to you, 1 Thatched Cottage with its uninterrupted views is an ideal holiday home. This 19th Century semi-detached property combines old ...
7 nights from £688 *
7 nights from £759
Barton Manor Lake Cottage
35812 bedroom, dog friendly holiday cottage near the beach in East Cowes, Isle of Wight.
Steeped in history Barton Manor is of great significance to the Isle of Wight’s heritage, situated adjacent to Osborne House and part of the original estate. The grand driveway lea...
7 nights from £759
7 nights from £783
Apt 1 Springfield Court
35752 bedroom self catering apartment near the beach in Seaview.
Apt 1 Springfield Court is a luxurious, ground floor apartment, set in an exclusive development in the picturesque village of Seaview. It would suit a small family or a couple in n...
7 nights from £783
We’re here to help you find your perfect place to stay 7 days a week.
Open 7 days a week
Call our office on 01326 555555, email hello@classic.co.uk or click on the live chat button in the bottom right of the screen to talk directly to someone who can help with choosing your holiday. If you have any questions or need a hand with the booking process, we’re happy to help.
After booking your holiday with us, you’ll receive your holiday details two weeks before your holiday. This also includes our emergency out of hours phone number for when the office is closed, so we’re never more than a phone call away!
7 nights from £888
Starboard Side
47362 bedroom, dog friendly holiday cottage near the beach in Cowes, Isle of Wight.
This gorgeous and beautifully presented cottage is within walking distance of lovely Gurnard beach and has wonderful sea views from the first floor main bedroom. The owner of Starb...
7 nights from £888
7 nights from £908 *
Bay View
39022 bedroom, rural holiday apartment near the beach in Freshwater, Isle of Wight
Perched above the stunning Freshwater Bay, this elegant contemporary apartment offers breathtaking views of the scenic coastline and the ultimate spot for refreshing seaside dips. ...
7 nights from £908 *
