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 1343 luxury self-catering cottages for the October half term
7 nights from £675
Cuckoo Cottage
61412 bedroom, dog friendly cottage near the beach in St Agnes, Cornwall.
This bijou bolthole has luxurious interiors and is set in a fabulous location in the heart of St Agnes. Cuckoo Cottage is a charming, terraced cottage which has been thoughtfully c...
7 nights from £675
7 nights from £1400
Rheidiol Cottage
61493 bedroom, dog friendly holiday cottage near the beach in St Davids.
Let your next coastal adventure begin in splendid Rheidiol Cottage. Set in the heart of enchanting St Davids, on Wales' breathtaking Pembrokeshire coast, soak up the mystical vibe,...
7 nights from £1400
7 nights from £1022
The Woodlands
61354 bedroom, dog friendly self catering cottage near Great Malvern.
A traditional bolthole with contemporary flair is just what you will find at The Woodlands. Cosseted in over two acres of gardens and an easy stroll to the river, this is a luxury ...
7 nights from £1022
7 nights from £925
Witts End
61362 bedroom self catering cottage near Chipping Norton.
Tucked away in a quintessential Cotswold village, Witts End is a charming holiday cottage that promises a truly tranquil escape. With a welcoming village pub just at the end of the...
7 nights from £925
British Travel Awards 2025
Best company for UK holiday home rentals
7 nights from £1022
Holly Tree
61454 bedroom, dog friendly self catering cottage near York.
Set in the historic village of Myton on Swale, which was mentioned in the 1086 Domesday book and home to a charming historic 19th Century cast Iron bridge, Holly Tree offers an idy...
7 nights from £1022
7 nights from £1661
The Rathgowry
61465 bedroom holiday cottage with sea views in Falmouth, South Cornwall.
Just moments from Gyllyngvase beach in Falmouth, this grand semi-detached, townhouse offers an elegant blend of early 20th Century design and contemporary luxury. Formerly owned by...
7 nights from £1661
7 nights from £690 *
Trelynden
61584 bedroom, dog friendly cottage near the beach near Marazion.
Set in the heart of the much-loved village of Goldsithney, Trelynden is an impressive granite faced home full of space, warmth and so comfortable for eight lucky guests. This prope...
7 nights from £690 *
The Hideaway
211Stylish seaside hideaway with hot tub and stunning sea views
Perched above the coast just outside Laxey, The Hideaway is a beautifully designed studio-style annex made for slow mornings, sea air, and romantic escapes. With uninterrupted view...
7 nights from £468 *
Ty Pinc
61423 bedroom, dog friendly holiday cottage near the beach in Cardigan.
Nestled in the quiet village of St Dogmaels (Llandudoch), one of Pembrokeshire's most picturesque coastal villages, Ty Pinc invites you in with warmth, offering a carefully restore...
7 nights from £468 *
7 nights from £1040 *
Tregoose Farmhouse
60855 bedroom thatched cottage with sea views near Truro, South Cornwall.
This enchanting 'picture postcard' cottage in the tranquil setting of Devoran is the kind of place where you arrive and then instantly relax. Surrounded by beautiful Cornish countr...
7 nights from £1040 *
Be in the know… Sign up to our newsletter for holiday inspiration, offers and all things Classic.
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.