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 109 available cottages to find your perfect one, or get in touch for more information.
109 self-catering cottages on the Isle of Wight
7 nights from £843
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 £843
7 nights from £848
Blackberries
35833 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
A warm Isle of Wight welcome awaits you at Blackberries, a pretty coastal cottage which offers a peaceful escape for families, small groups or couples alike, in the delightful sail...
7 nights from £848
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 £1400
Creekside
35884 bedroom, dog friendly holiday cottage with sea views in Wootton, Isle of Wight.
Creekside is a fabulous waterfront property that makes a wonderful choice of holiday home at any time of the year. This stunning detached house, set on the banks of Wootton Creek, ...
7 nights from £1400
7 nights from £584
East Gull Sands
35953 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
Seaview is a much sought-after and very charming village on the Isle of Wight and East Gull Sands sits in a magical position overlooking the beach, just a short stroll away from th...
7 nights from £584
7 nights from £564
Faithfull Cottage
36002 bedroom, dog friendly holiday cottage near the beach in St Helens, Isle of Wight.
Faithfull Cottage is a welcoming retreat situated within two miles distance of St Helens village on the Isle of Wight, as well as a gorgeous beach, RSPB Nature Reserve and the vill...
7 nights from £564
7 nights from £936
Garsdon
36044 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
This lovely bright and spacious detached house located on a quiet lane in Seaview is just a ten minute stroll from the beautiful beach at Seagrove Bay. With a charming large enclos...
7 nights from £936
7 nights from £722
Lawn End
36173 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
Tucked away in a quiet corner of the delightful village of Seaview, Lawn end is a cosy island retreat, tastefully furnished to offer contemporary living for families or a group of ...
7 nights from £722
7 nights from £736 *
Lucaya
36214 bedroom self catering cottage near the beach in Ryde, Isle of Wight.
Welcome to Lucaya, a smart town house for eight set over three floors, a great space with a pretty enclosed rear patio and lawn, the ideal stay for a family looking for a seaside b...
7 nights from £736 *
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7 nights from £1272 *
Neptune Cottage
36364 bedroom, self catering cottage near the beach in Seaview, Isle of Wight.
Just a few steps from your front door to the sea, this stunning newly refurbished seafront cottage is an exceptional place to stay in Seaview. With many of the rooms boasting wonde...
7 nights from £1272 *
7 nights from £1372
Orchard House
36414 bedroom, dog friendly holiday cottage near the beach in Bembridge, Isle of Wight
Orchard House is a wonderful property for an extended family looking for a sprawling holiday home near the beach in Bembridge. The downstairs living areas are inviting - no doubt t...
7 nights from £1372
