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.
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 169 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
169 self-catering cottages on the Isle of Wight
Solent Peek
39653 bedroom, dog friendly holiday cottage near the beach in Freshwater, Isle of Wight
Welcome to Solent Peek, a lovely comfortable home in Totland on the West Coast of the Island. As the name suggests, there is sea view from the first floor master bedroom and it is ...
Price per week £495 - £695
Turnstone
38283 bedroom self catering cottage in East Cowes, Isle of Wight
Turnstone is a beautifully designed, newly built town house situated overlooking the River Medina on the north coast of the island and within walking distance of Osborne House. Fro...
Price per week £495 - £640
Old Railway Cottage
39903 bedroom self catering cottage near the beach in Bembridge, Isle of Wight
This charming cottage is tucked away down an unmade road just off Bembridge Harbour, within walking distance of Bembridge village centre. The front and rear gardens of Old Railway ...
Price per week £495 - £715
9 Crown Court
41693 bedroom self catering cottage with sea views in Cowes, Isle of Wight.
Right in the heart of the bustling sailing town of Cowes, 9 Crown Court offers great accommodation with a stunning roof terrace boasting uninterrupted views across the rooftops to ...
Price per week £500 - £725
Don’t miss out; reserve your favourite 2019 holiday cottage for just £30
Reserve your 2019 holiday
Our portfolio gets better year after year, with all the old favourites and some stunning new additions, so get in there quick and reserve your preferred dates for only £30.
Pick a place close to the coast for that year-round holiday vibe, or book a holiday townhouse to be close to every convenience. Escape to the country for peace and quiet or take to the moors for walks through wide open spaces, we’ve got plenty of holiday cottages for you to choose from for next year.
Reserve next year's holiday in advance to give you peace of mind and put off paying your deposit till after this summer (5th November). That way you know your preferred dates are yours for the choosing and you can get on with enjoying the rest of this year's holiday (before looking forward to the next!).
Primrose Cottage
36453 bedroom self catering cottage near the beach in St Helens, Isle of Wight
Primrose Cottage is a fully modernised and beautifully furnished Victorian three bedroom cottage situated just off the green in St Helens and offering everything you might need for...
Price per week £504 - £707
3 Quay Rocks
35453 bedroom self catering apartment near the beach in Seaview.
Perched right on the waterfront opposite Seaview beach, 3 Quay Rocks has unrivalled views of the attractive seafront and beyond, out to the ships passing by on the Solent. The apar...
Price per week £510 - £690
6 Coastguard Cottages
35583 bedroom, dog friendly holiday cottage near the beach in Brook, Isle of Wight.
Formerly the officer's quarters of the coastguard station, 6 Coastguard Cottages has been beautifully decorated and offers a wonderful holiday home in Brook. This period property h...
Price per week £511 - £772
Portholes
40073 bedroom self catering cottage near the beach in Seaview, Isle of Wight
Tucked away down a quiet side street in the idyllic village of Seaview, Portholes is a fantastic holiday home just minutes away from the sea. All within walking distance from your ...
Price per week £520 - £795
1 Barton Lodge
35023 bedroom, dog friendly cottage near the beach in East Cowes, Isle of Wight.
This truly lovely holiday home, with a wood-burner, is a great choice whatever the season. 1 Barton Lodge is a beautiful property which has been lovingly restored with your comfort...
Price per week £544 - £753
Little Bramley
40393 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight
A lovely three bedroom house in the heart of Seaview village within a few minutes walk to the seafront and Seaview Yacht Club. Beautifully decorated throughout with an open plan li...
Price per week £550 - £795
We are Gold accredited with the Green Tourism Business Scheme.
Green Tourism Business Scheme
As a company, we look across our business and try to make sustainable changes and decisions. From using recycled paper in our printers to putting in measures for using less energy in our offices, we keep an eye on our impact on the environment.
Beyond our offices, we have passed on the same ethics to our holiday cottage owners by setting up our own Green Scheme that they can join. Each property has to tick off a certain number of actions to be included in the scheme, many of which go above and beyond the GTBS requirements.