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 1354 luxury self-catering cottages for the October half term
7 nights from £1300
Magical Barn
59962 bedroom self catering cottage near Haltwhistle.
Magical Barn is nestled on the edge of the Dark Sky Park in Northumberland amid green hills and woodland and from the moment you step out of your car and turn the corner to catch y...
7 nights from £1300
7 nights from £1300
Magical Cottage
59972 bedroom self catering cottage near Haltwhistle.
Situated within a delightful courtyard surrounded by verdant landscapes, you'll find Magical Cottage. This beautifully converted single-storey former outbuilding, pairs its agricul...
7 nights from £1300
The Old Parsonage Barn
192A peaceful countryside hideaway for two beneath dark Manx skies
Tucked away in the quiet heart of St Judes, The Old Parsonage Barn is a peaceful countryside retreat designed with two in mind. Set against wide open fields and beneath some of the...
7 nights from £2771
Haske Barton
60806 bedroom thatched, dog friendly home in Crediton, South Devon.
Welcome to Haske Barton, a beautiful 16th Century Devon Longhouse nestled in a quiet, countryside setting, with wonderful grounds and gardens to enjoy. This charming Grade II Liste...
7 nights from £2771
7 nights from £694
Upper Warren
60703 bedroom holiday cottage with sea views in St Mawes, South Cornwall.
Nestled in the heart of the charming harbourside village of St Mawes on the stunning Roseland peninsula, with beaches, cafes and independent shops just a stroll away, Upper Warren ...
7 nights from £694
7 nights from £490
Cwtch y Rhos
60861 bedroom self catering cottage near the beach in Fishguard.
Escape to Cwtch y Rhos for a romantic getaway. Nestling within walking distance of the centre of the historic coastal town of Fishguard and the picturesque harbour of Lower Town, e...
7 nights from £490
7 nights from £862 *
The Cygnet - Lodge 11
60442 bedroom self catering cottage near Chard, Somerset.
*Please note, short breaks of four nights or more may be available between January 2026 and the end of the Easter holidays. Please contact our bookings office for more information....
7 nights from £862 *
7 nights from £770
Glen Cottage
60762 bedroom, dog friendly cottage with sea views near Dartmouth.
Welcome to Glen Cottage, a beautiful Grade II Listed thatched cottage which oozes charm and character. Nestled in the heart of one of the South Hams picture-perfect coastal village...
7 nights from £770
We’ve been raising the standards of self catering holidays since 1977.
Our family ethos
Tony and Clare Tregoning started the business back in 1977 and their dedication to quality and excellence is at the heart of everything we do. Tony is sadly no longer with us, but we still adhere to their original ethos of finding holiday homes we would like to stay in and have slowly grown the company to find the best picks of properties across the counties. Plus Clare still drops in to keep us on our toes.
As an independent, family-run company, we wouldn’t expect you to stay anywhere we wouldn’t want to stay ourselves. And we’re pretty picky. We want you to walk into your handpicked holiday home and say ‘wow’, sit back and relax.
7 nights from £1018
East Cottage
60872 bedroom self catering cottage near Tenby.
Immersed in idyllic woodland amongst rolling meadows in a secluded corner, East Cottage offers the perfect tranquil Welsh retreat, yet is only seven miles from the heart of bustlin...
7 nights from £1018
7 nights from £465
Elfie
6062Fairytale cabin with wood-burner and landscape views in Shropshire.
Nestled in the heart of the Shropshire Hills, this unique hideaway is a fairytale getaway, come to life. Only five miles from the Welsh border, this otherworldly structure could ha...
7 nights from £465
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.
