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 1428 available cottages. Read more
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.We've got 1428 holiday cottages available for October
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
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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 £543
Number 67
61311 bedroom, dog friendly apartment near the beach near Falmouth.
A beautifully stylish abode offering the ultimate retreat; just a 10 minute walk into Falmouth town centre or to the beach, this gorgeous ground floor apartment has been thoughtful...
7 nights from £543
7 nights from £1120
Dormy House
60843 bedroom, dog friendly holiday cottage near the beach in Hunstanton.
Dormy House is single-storey beach house, nestled in an idyllic spot, just moments away from the stunning beaches of this much-loved village, along the north west Norfolk coastline...
7 nights from £1120
7 nights from £505
The Bothy
61251 bedroom, dog friendly self catering cottage near Skipton.
If you are craving a cosy getaway for two or a quiet friend's weekend, The Bothy is a great choice. It is a traditional, restored stone cottage sitting right in the heart of the de...
7 nights from £505
From £900 per night
The Retreat
61215 bedroom, dog friendly self catering cottage near Crickhowell.
The spellbinding beauty of the Bannau Brycheiniog (Brecon Beacons) are calling you for your next celebration or larger get-together. Escape to the hills at the exquisite The Retrea...
From £900 per night
7 nights from £960 *
12 Castle Street
61304 bedroom, dog friendly self catering cottage near Ruthin.
Step into a world of timeless elegance and sheer comfort in 12 Castle Street, where classic charm meets modern luxury and pure relaxation. Escape to this superbly renovated Victori...
7 nights from £960 *
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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 1428 holiday cottages for October for you to choose from.