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.101 luxury cottages for October half term on the Isle of Wight
7 nights from £1521 booking fees included
St Hubert's Lodge
60573 bedroom, dog friendly self catering cottage near Yarmouth.
Surrounded by tranquil countryside on the edge of the Isle of Wight National Landscape and close to the charming seaside island towns of Yarmouth and Cowes, St Hubert's Lodge is a ...
7 nights from £1521
7 nights from £1168 booking fees included
Grey Gulls
61594 bedroom dog friendly self catering cottage with sea views in Seaview.
This beautifully presented, semi-detached, three-storey townhouse is set in the sought-after village of Seaview, just a stone's throw away from stunning beaches with crystal clear ...
7 nights from £1168
Readymade beds and fluffy towels; this simple but appreciated welcome is standard with us.
Towels and readymade beds
All of our cottages provide bed linen and towels as standard, with a change of bedding included for holidays of two weeks or more. You’ll also find a fresh change of towels for each week (for in the house only, please bring your own for the beach) and tea towels a-plenty.
The beds will be readymade and waiting for you on arrival so you can simply sink into comfort and relax straight into your holiday.
7 nights from £513 booking fees included
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 £513
7 nights from £886 booking fees included
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 £886
British Travel Awards 2025
Best company for UK holiday home rentals
7 nights from £1006 * booking fees included
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 £1006 *
7 nights from £1236 * booking fees included
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 £1236 *
7 nights from £549 booking fees included
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 £549
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20% off
25 Jul 2026 - 1 Aug 2026
£810.00 £711.00 booking fees included
7 nights from £886 booking fees included
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 £886
7 nights from £1144 booking fees included
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 £1144
7 nights from £807 booking fees included
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 £807
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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 101 cottages available for October half term and find your favourite one.
