November on the Isle of Wight
Across the Isle of Wight we have a collection of 90 self-catering cottages for November. Offering wide variety and consistent quality, you can spend your November break exactly the way you please surrounded by home comforts and modern luxuries. Pour through our available properties and let your imagination run wild, a dream retreat is just around the corner. Read more
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.90 cottages for November on the Isle of Wight
7 nights from £547
Bay Cottage
61502 bedroom self catering cottage near the beach in Cowes.
Tucked away in the charming village of Gurnard on the northwest coast of the Isle of Wight, this cosy two bedroom cottage offers a relaxed coastal lifestyle, complete with a pretty...
7 nights from £547
7 nights from £805
Wickings
61013 bedroom, dog friendly holiday cottage near the beach in Ventnor.
Nestled in the sheltered seaside town of Ventnor, blessed with its own gentle microclimate, this wonderfully welcoming and peaceful retreat is perfect for relaxing, unwinding and s...
7 nights from £805
7 nights from £755 *
Little Field
61233 bedroom, dog friendly holiday cottage near the beach near Ryde.
Tucked away on a quiet road, Little Field has been lovingly built by the owners and offers guests a peaceful and tranquil retreat with oodles of space and modern living. Situated o...
7 nights from £755 *
7 nights from £861 *
The Police House
60514 bedroom, dog friendly holiday cottage near the beach in Seaview.
Perfectly situated in the heart of the charming village of Seaview on the stunning east coast of the Isle of Wight, The Police House is a delightful, detached holiday home located ...
7 nights from £861 *
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7 nights from £486
Seascape
59442 bedroom self catering apartment with sea views in Ventnor, Isle of Wight.
Located in the cosmopolitan town of Ventnor within a Victorian townhouse, Seascape is a modern two-bedroom, ground floor, apartment with spectacular sea views overlooking the bay. ...
7 nights from £486
7 nights from £1046
Maybury
59913 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
Your dream coastal escape awaits in Seaview! Escape to elegant Maybury and stay in this beautifully styled home with sandy beaches and village amenities on your doorstep. This blis...
7 nights from £1046
7 nights from £805
Fenders
59873 bedroom, dog friendly cottage near the beach in Totland.
Your memorable Isle of Wight coastal escape awaits at Fenders, a beautifully appointed single-storey retreat, situated just moments from the picturesque beach at Totland Bay. Tucke...
7 nights from £805
7 nights from £1058
Sun Lodge
58534 bedroom, dog friendly holiday cottage with sea views in Ventnor.
Step back in time and immerse yourself in the historic charm of Ventnor at this elegant Isle of Wight retreat with mesmerising sea views and generous spaces for a truly relaxing fa...
7 nights from £1058
7 nights from £1061
Pucks Oak
56984 bedroom, dog friendly holiday cottage with sea views in Seaview.
Within moments of the seafront at Seaview, with off-street parking and a lovely garden, semi-detached Pucks Oak is a great home-from-home to enjoy with friends and family. With the...
7 nights from £1061
7 nights from £721
Bentinck
57243 bedroom cottage near the beach in Ventnor.
With everything you could wish for on your doorstep for a blissful Isle of Wight holiday experience with family or friends, Bentinck is a great base to explore all that this Island...
7 nights from £721
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.
Whether you are looking for a novel way to spend Bonfire Night, hoping to make the most of the island's empty beaches or would like some serious rest and relaxation with your loved ones, we'll help you pave the way to an idyllic retreat. With autumn moving into winter and an atmospheric cheer in the air, you can look forward to lazy mornings, revitalising days out and evenings in in front of the fire. Browse through our available cottages and see what piques your interest. At Classic Cottages, we have learnt a thing or two about holidays over the years and understand the importance of accommodation in making or breaking your experience. That's why all of our properties are handpicked and personally inspected so your holiday is the best it can be. All you have to do? Enjoy.
