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 £792 *
Valdora
49593 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
Perfectly situated in the heart of the charming village of Seaview, Valdora is a gorgeous holiday retreat, beautifully styled to offer the very best in contemporary living. Seaview...
7 nights from £792 *
7 nights from £625
19 Seaview Bay
49261 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
Escape to the delights of 19 Seaview Bay to enjoy a slice of stunning Island coastline, a gentle stroll around the pretty local shops, relax with an afternoon tea at Seaview Hotel ...
7 nights from £625
Choose our flexible booking option and have the ability to cancel anytime.
7 nights from £1229 *
Oystercatcher
48693 bedroom luxury houseboat in Bembridge, Isle of Wight.
Set in picturesque Bembridge Harbour with far reaching views out to the Solent, Oystercatcher is a luxurious houseboat, beautifully furnished and just waiting to welcome you on boa...
7 nights from £1229 *
7 nights from £526
Westhill View
48822 bedroom self catering cottage near the beach in Shanklin, Isle of Wight.
With the golden sands of Shanklin beach a short walk away, this lovely holiday home sits in the heart of town, perfect for traditional days by the seaside and within easy reach of ...
7 nights from £526
7 nights from £1296
9 The Ruskins
48653 bedroom self catering cottage near the beach in Bembridge, Isle of Wight.
This delightful family holiday home can be found just a short stroll from the beautiful beaches of Bembridge and a wonderful array of traditional shops and restaurants. Light fille...
7 nights from £1296
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20% off
23 Nov 2024 - 30 Nov 2024
£1114.00 £891.20
7 nights from £648
Buckland Cabin
48531 bedroom cabin near the beach in Seaview, Isle of Wight.
Tucked away just off the High Street in Seaview, this recently renovated and beautifully presented cabin is ideal if you are seeking a romantic hideaway for two. Step inside th...
7 nights from £648
7 nights from £3620
Cara Cottage
48465 bedroom, dog friendly holiday cottage near the beach in Bembridge, Isle of Wight.
Welcome to Cara Cottage, a stunning detached property located in the heart of Bembridge village. This eye-catching holiday home with soft pink 'Spanish inspired' exterior is beauti...
7 nights from £3620
7 nights from £806 *
Daisy Cottage
48242 bedroom, dog friendly holiday cottage near the beach in Bembridge, Isle of Wight.
Daisy Cottage is a lovely cosy and welcoming mid terrace cottage nestled in the heart of Bembridge. Located in one of the most desirable areas to live in on the Isle of Wight, this...
7 nights from £806 *
Arrive at your handpicked holiday home safe in the knowledge it’s been fully inspected.
Quality inspections
We check our holiday homes to ensure that everything is up to our high standards for your holiday, from provision of our above standard minimum inventory to how fluffy the towels are, we make sure you’ll have a comfortable stay.
Hardworking teams of housekeepers will have the place spick and span, ready for your arrival, so when you get there you can just relax.
7 nights from £973
Old Bembridge House
47913 bedroom, dog friendly holiday cottage near the beach in Bembridge, Isle of Wight.
Tucked away on an unmade track just a few yards from the sea and Bembridge Yacht club, Old Bembridge House has all the makings of a perfect holiday idyll. Laid across three floors,...
7 nights from £973
7 nights from £2128
Harbour View
47314 bedroom self catering cottage with sea views in Ryde, Isle of Wight.
Escape to the Isle of Wight for a blissful coastal retreat at Harbour View, an impressive Grade II Listed townhouse with stunning sea views, spread over three floors, and with the ...
7 nights from £2128
