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 1436 available cottages. Read more
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.We've got 1436 holiday cottages available for October
7 nights from £562
Bramble Cottage
61391 bedroom, dog friendly cottage near the beach in Kingsand, Cornwall.
This delightful bolthole is the perfect escape for solo adventurers and couples looking for a charming, bijou retreat in one of Cornwall's most beautiful pockets. Set in the breath...
7 nights from £562
7 nights from £496
Azure Sky
6116Shepherds Hut with wood-fired hot tub and outdoor bath near Tintagel, Cornwall
Nestled within a 30-acre working farm in the scenic north Cornwall countryside, Azure Sky, an idyllic dog-friendly shepherd’s hut, is just the place for that peaceful escape you’ve...
7 nights from £496
7 nights from £538 *
Minnie's Cottage
61262 bedroom, dog friendly cottage near the beach near Bridport.
Minnie's Cottage is a cosy quintessential thatched cottage in the beautiful coastal village of Burton Bradstock. Situated in the heart of the village and just half a mile from the ...
7 nights from £538 *
7 nights from £441
Ketch
61142 bedroom, dog friendly apartment with sea views in Portscatho.
With far reaching views across Gerrans Bay and an easy stroll to the centre of the charming village of Portscatho on the Roseland peninsula, Ketch is a rather lovely first floor ap...
7 nights from £441
British Travel Awards 2025
Best company for UK holiday home rentals
Reayrt Ny Marrey
210Charming Manx cottage in the picturesque village of Kirk Michael
Nestled on the island's western corner, Reayrt Ny Marrey is perfectly placed in Kirk Michael, known for its captivating shorelines, long sandy beaches, and dramatic woodland and gl...
7 nights from £707 *
Treglindon
61003 bedroom cottage with sea views near Crackington Haven, North Devon.
Set high above the north Cornwall coastline in the peaceful hamlet of Rosecare, Treglindon is a beautifully spacious holiday home offering breathtaking panoramic views across rolli...
7 nights from £707 *
7 nights from £621
Shillings Cottage
61401 bedroom, dog friendly holiday cottage near Honiton, South Devon.
Sat on a gentle hillside, this pretty flint cottage with a glorious outdoor seasonal swimming pool and stunning gardens is perfect for those looking for peace and tranquility. Nest...
7 nights from £621
7 nights from £838
Mr Brightside
61223 bedroom, dog friendly holiday cottage near the beach in Hunstanton.
This semi-detached townhouse is perfectly placed to enjoy a traditional Norfolk seaside holiday; create special memories with loved ones in this well thought-out holiday home which...
7 nights from £838
7 nights from £823
Wickings
61013 bedroom, dog friendly holiday cottage near the beach in Ventnor.
Nestled in the sheltered seaside town of Ventnor, blessed with its own gentle microclimate, this wonderfully welcoming and peaceful retreat is perfect for relaxing, unwinding and s...
7 nights from £823
7 nights from £981
7 Bay View
60693 bedroom, dog friendly cottage near the beach in Croyde, Devon.
Set in the heart of the traditional coastal village of Croyde, this stylish upside-down holiday home offers the perfect base for a memorable north Devon escape. With endless golden...
7 nights from £981
Be in the know… Sign up to our newsletter for holiday inspiration, offers and all things Classic.
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 1436 holiday cottages for October for you to choose from.