Holiday Cottages for October on the Isle of Wight
Although you may not expect it to be so, the Isle of Wight often benefits from lots of sunshine and mild weather well into October. With the sea warmed from months of the sun's rays and the atmosphere calm, it is a truly wonderful time of year to explore the island. Book a luxury retreat and enjoy the island from a home-from-home this October.Read more
Rolling countryside bearing colours of rust, deep red and burnt orange, long sandy beaches bathed in warm sunshine and quiet towns and promenades: this is October on the Isle of Wight. However you'd like to spend your holiday and whoever you'd like to share it with, the Isle of Wight offers a beautiful playground where adventure beckons. With as many opportunities to relax as to explore, you can spend your days exactly as you please and return to your own slice of paradise. At Classic Cottages, we pride ourselves on marketing only the highest quality self-catering accommodation around. Handpicking and personally inspecting each property, we make sure each meets exacting standards so your whole holiday is the best it can be. Browse our 149 available cottages to find your perfect one, or get in touch for more information.
With 200 ferries daily, our hassle free booking service makes your trip to the island plain sailing
149 self-catering cottages on the Isle of Wight
7 nights from £250
Grace Cottage
42091 bedroom, dog friendly holiday cottage near the sea near Ventnor, Isle of Wight
This gorgeous barn conversion is set within the grounds of the stunning North Grounds Farm, just outside the village of Chale Green on the southern side of the Island. Laid over on...
7 nights from £250
7 nights from £300
Little Barn Retreat
41871 bedroom, rural self catering cottage in Newport, Isle of Wight
This absolutely gorgeous barn conversion is the perfect place for a couple's holiday, located on the Durton Farm Estate in the centre of the Island. Lovingly refurbished by the own...
7 nights from £300
Need more time? Reserve any cottage for up to 24 hours before booking.
24hr no commitment reservations
You can reserve your holiday dates on your favourite cottage for up to 24 hours. You might need to check with other guests in your party or simply consider whether this cottage is right for your holiday, either way we’re happy to give you the time to step away and mull over your options before paying a penny.
We’ll send you a reminder to see if you want it or not so you won’t lose out. Take time to think it over, you don’t have to rush your decision. Have a cup of tea and when you’re ready, hit the button to book your holiday and start looking forward to it.
7 nights from £301
Berryl Mead View
39061 bedroom self catering cottage near Ventnor, Isle of Wight
Located in a rural village setting, Berryl Mead View is a delightful home from home cottage with plenty of space, well equipped throughout and extremely comfortable living room wit...
7 nights from £301
7 nights from £360
The Cadogan Apartment
36671 bedroom self catering apartment near the beach in Shanklin, Isle of Wight.
Sitting within a beautifully converted Victorian villa, The Cadogan Apartment offers a high standard of accommodation for a couple or lone traveller looking for a coastal break. Gu...
7 nights from £360
7 nights from £316
62 Buddleia Cottage
35662 bedroom self catering cottage near the beach in Seaview.
Located in a small waterside development on the edge of Seaview, 62 Buddleia Cottage is a pretty beach bungalow offering comfortable accommodation, for a couple or small family, in...
7 nights from £316
-
20% off
21 Sep 2019 - 28 Sep 2019
£342.55 £274.04
7 nights from £360
The Worsley Apartment
36821 bedroom self catering apartment near the beach in Shanklin, Isle of Wight.
Offering a high standard of accommodation, the Worsley Apartment is a ground floor apartment housed within Shanklin Villa, a beautifully converted Victorian building. With a separa...
7 nights from £360
7 nights from £241
The Crows Nest
36702 bedroom self catering apartment with sea views in Seaview, Isle of Wight.
The Crows Nest is a second floor apartment at the top of a Victorian property in the historic village of Seaview. A family looking for a convenient base from which to enjoy the Isl...
7 nights from £241
-
20% off
27 Sep 2019 - 4 Oct 2019
£300.95 £240.76
7 nights from £272
Faithfull Cottage
36002 bedroom, dog friendly holiday cottage near the beach in St Helens, Isle of Wight.
Faithfull Cottage is a lovingly restored, pretty mid-terrace cottage which enjoys a rear garden and countryside views on the outskirts of St Helens. This comfortable cottage is set...
7 nights from £272
-
20% off
28 Sep 2019 - 5 Oct 2019
£339.97 £271.97
Our guests rate us 4.8/5 on Feefo, the independent review site.
Feefo ratings
Our latest feedback on Feefo:
7 nights from £284
2 Bermuda
35172 bedroom self catering apartment with sea views in Seaview.
Not far from the sea you will find 2 Bermuda, a bright, neutrally decorated flat that is perfect for a family with children or a couple. The location is what makes this flat so spe...
7 nights from £284
-
20% off
28 Sep 2019 - 5 Oct 2019
£354.78 £283.83
7 nights from £301
53a Howgate Road
37492 bedroom, dog friendly apartment near the beach in Bembridge, Isle of Wight.
This two bedroom apartment in Bembridge is small but perfectly formed. Lovingly restored by the owners, 53a offers a perfect base for a family with a light and airy double bedroom ...
7 nights from £301