Holiday Cottages for October
Booking a holiday cottage in October may sound like a winter break, but summer often extends its stay and graces October with glorious sunshine and warm weather. With quiet weeks and an opportunity to take the kids away for half term, there are lots of things to look forward to however you'd like to spend your holiday. Get started and browse our 1317 available cottages. Read more
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.We've got 1317 holiday cottages available for October
7 nights from £660 booking fees included
New Mill
61912 bedroom, dog friendly holiday cottage near Bovey Tracey, Dartmoor.
Welcome to this rather unique holiday retreat. New Mill is a rather deceiving name for this Grade II Listed watermill, which boasts many stunning original features, lovingly preser...
7 nights from £660
7 nights from £910 booking fees included
Hillside View
62153 bedroom, dog friendly holiday cottage near Tavistock, Dartmoor.
Tucked away in the glorious Tamar Valley, Hillside View is a rather special holiday retreat where peace, beautiful countryside and the great outdoors are right on your doorstep. Wi...
7 nights from £910
Reserve your 2027 holiday for just £40.00
Find out more7 nights from £789 booking fees included
Ruska
6209Luxury cabin for two with an outdoor bath, privately nestled in the Forest of Dean.
Sitting in the Gloucestershire countryside, this lakeside retreat for two offers a peaceful and romantic getaway. This gorgeous cabin has been lovingly handcrafted with luxury in m...
7 nights from £789
Greystones at Ago's Leap
221Impressive Douglas home with private gardens and tennis court
Set along Quarterbridge Road in Douglas, Greystones is a striking and spacious home offering an impressive place to stay within easy reach of the Island's capital. Beautifully p...
British Travel Awards 2025
Best company for UK holiday home rentals
7 nights from £796 booking fees included
Goaf Cottage
62042 bedroom, dog friendly self catering cottage near Whitby.
In a county of hills, dales and sandy beaches, you will find the moors village of Glaisdale and nestled in a sleepy lane sits Goaf Cottage, an old farm building converted into a go...
7 nights from £796
Ballacosney Cottage
219Stylish Laxey cottage with private gym and sauna
Tucked away up a peaceful lane above Laxey, Ballacosney Cottage is a beautifully renovated retreat designed with relaxing island stays in mind. Fresh, modern and filled with natura...
7 nights from £588 booking fees included
Rubena Cottage
62002 bedroom, dog friendly cottage near the beach in Port Isaac.
A mere hop, skip and a jump from the water's edge, this absolute gem of a cottage has been restored with exquisite care, creating a most desirable retreat that's perfect for warm s...
7 nights from £588
7 nights from £1085 booking fees included
Hooper's House
62034 bedroom self catering cottage in Gloucester.
Hooper's House is a centuries-old property sitting in harmony with the historic buildings of Gloucester Cathedral but with a contemporary interior vibe, mixing traditional and mode...
7 nights from £1085
7 nights from £861 booking fees included
St Peter's House
62022 bedroom self catering cottage in Gloucester.
Set within Gloucester Cathedral's grounds with a magnificent glimpse of the Cathedral spires from the impressive staircase, St Peter's House enjoys a truly amazing location. A hous...
7 nights from £861
Round Table House
218A unique countryside retreat with breathtaking southern views
Round Table House stands high above the rolling countryside of Ronague, a remarkable retreat where contemporary style meets the character of a much-loved home. Its elevated positio...
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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!
We’re not promising, but it's not uncommon to be able to sit on the beach in October enjoying bright sunshine, particularly hot in a sheltered corner. And at this time of year you can also bring the dog with you as the doggy beach ban is lifted in September. Bring your bag, ball and a bowl for water, and you could spend hours playing games and relaxing on the beach, occasionally dipping your toes in the sea to cool off. October is also a great time to explore gardens and woodlands as they put on golden autumnal coats for their end of year display. Bring the family during October half-term to relive memories of a spent summer or indulge in a luxury short break before the winter kicks in. We have 1317 holiday cottages for October for you to choose from.