Cottages for October Half Term
Gently releasing its grip on summer, October often enjoys warm weather and soft sunshine. Embrace the t-shirt weather a little longer and enjoy a self-catering retreat this October half term. From quaint one-bed cottages to spacious retreats big enough for all the family, we can help you piece together the perfect autumn holiday in a luxury cottage. Take a look at our collection and secure your favourite one today. And don't forget, once you've paid your deposit, you can pay the remaining balance off in monthly instalments - find out more here. Read more
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.We have 1333 luxury self-catering cottages for the October half term
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
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 £822 *
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 £822 *
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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Best company for UK holiday home rentals
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 *
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
We’re here to help you find your perfect place to stay 7 days a week.
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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!
October can be the most colourful month of the year, with trees parading their final flourish before stripping bare for the winter. Take the kids on a half term holiday to remember and soak up the last hints of green. A day out to a public garden might not be first on the children's list of things to do but running through tunnels lined with golden leaves and feeling the crunch underfoot will soon have them jumping in leafy mounds with excitement. The sea has a magical quality, reflecting the October sky and sparkling on the horizon. It doesn't matter if the weather takes a turn for the wintery worse, as a good storm will liven up any school holiday - stand safely back from the sea and feel the salty spray. Once you've finished exploring, return to your very own private retreat and relax in total comfort.