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 162 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
162 self-catering cottages on the Isle of Wight
7 nights from £587
Bay Cottage
40823 bedroom self catering cottage near the beach in Seaview, Isle of Wight
Bay Cottage is a lovely three bedroom detached property on the outskirts of Seaview village, located in Seagrove Manor Road, a quiet spot yet just a few minutes walk into the villa...
7 nights from £587
7 nights from £592
Shore House
37783 bedroom self catering cottage with sea views in Seaview, Isle of Wight
A seaside sanctuary, Shore House is a three-storey beautifully decorated house, with its own private heated swimming pool. Making the most of the far reaching views over the Solent...
7 nights from £592
7 nights from £595
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...
7 nights from £595
7 nights from £600
Greenacres Farm House
41903 bedroom, rural self catering cottage in Newport, Isle of Wight
This property is a truly idyllic cottage situated in the grounds of a farm, with stunning countryside views and a lovely garden. This is what you would describe as holiday heaven. ...
7 nights from £600
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 £600
Merivale
42404 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight
This lovely, light and spacious detached house located on Fairy Road in Seaview, just a short stroll from the seafront, makes a fantastic base for a wonderful holiday on the Isle o...
7 nights from £600
7 nights from £600
Tidal Retreat
42243 bedroom, rural self catering cottage with estuary views near Newport, Isle of Wight
This stylish three-storey town house is located in the exclusive development of Island Harbour, with two balconies overlooking the busy marina and providing the perfect sun-trap to...
7 nights from £600
7 nights from £610
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...
7 nights from £610
7 nights from £623
1 Harbour Strand
35053 bedroom self catering cottage near the beach in Bembridge, Isle of Wight.
1 Harbour Strand is a town house with jaunty decor, attractive furnishings and interesting prints, including some of the owners own artwork. It offers a games-room, with table-tenn...
7 nights from £623
7 nights from £637
Raleigh Cottage
36473 bedroom self catering cottage near the beach in Seaview.
In a quiet position within a secluded courtyard in the village of Seaview, Raleigh Cottage is the perfect blend of old-world charm and contemporary comfort. It would suit a family ...
7 nights from £637
7 nights from £643
Fernsdale
40053 bedroom self catering cottage near the beach in Seaview, Isle of Wight
Right in the heart of Seaview village, this semi-detached property has been completely renovated, with a Skandi theme, to offer a wonderful place to stay on the Isle of Wight. With...
7 nights from £643
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.