Cottages for October Half Term on the Isle of Wight
Pack your bags and round up the kids, an autumn holiday on the Isle of Wight is beckoning. Giving you something special to look forward to this October half term, all of our Isle of Wight cottages perfectly combine homely touches with modern luxuries. Take a look through our collection and find the one just right for you. The holiday of a lifetime is but moments away. Read more
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.98 luxury cottages for October half term on the Isle of Wight
7 nights from £823
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 £823
7 nights from £944 *
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 £944 *
7 nights from £1173 *
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 £1173 *
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
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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 £823
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 £823
7 nights from £1081
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 £1081
7 nights from £744
48 Solent View
58283 bedroom self catering cottage with sea views in Seaview.
Just a short wander from the golden sands of Seagrove Bay and the quaint charm of Seaview village, this stylish holiday haven offers modern home comforts in an unbeatable location ...
7 nights from £744
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 £737
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 £737
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.
A holiday on the Isle of Wight provides stunning coast, beautiful countryside and lots to see and do. With October often hanging onto good weather post-summer, it is a great time to explore the island and take in the sights. Making the most of the daylight hours before nights draw in and book yourselves a luxurious break on the Isle of Wight. Even if the weather takes a turn for the worse, stormy days can be hugely atmospheric, particularly if you have a sea view cottage on the Isle of Wight. As well as a complete inventory, many of our cottages offer unique facilities too, like games rooms and wood burners, so you can enjoy a break from the rhythm of everyday life in total comfort and style. Look through our 98 cottages available for October half term and find your favourite one.
