Cornwall Cottages for October Half Term
Warm weather can extend well into winter in Cornwall, so try a luxury holiday cottage for October half term and try it out. With our range of properties offering wide variety and consistent quality, you are sure to find a holiday cottage to capture heart and mind. Watch the trees turn from green to gold and welcome autumn in style with your little ones by your side. Read more
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.589 self-catering cottages for October half term in Cornwall
7 nights from £602 * booking fees included
Woonsmith
61922 bedroom, dog friendly holiday cottage near Penzance, West Cornwall.
Escape to the peace and allure of the Cornish countryside at this beautifully renovated two bedroom cottage with its secluded, exclusive wild swimming lake just outside the pretty ...
7 nights from £602 *
7 nights from £621 * booking fees included
Admiral's Den
61692 bedroom, dog friendly apartment near the beach in Penzance.
Step into a piece of Cornish history at Admiral’s Den, a two-bedroom apartment occupying a wing of the magnificent Grade II Listed Georgian Nancealverne House. Set within 25 acres ...
7 nights from £621 *
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.
Nancealverne Estate
7 nights from £1387.59 booking fees included
7 nights from £766 * booking fees included
Apple Loft Cottage
61682 bedroom, dog friendly cottage near the beach in Penzance, Cornwall.
Nestled within 25 acres of enchanting grounds of historic Nancealverne House, Apple Loft Cottage is a beautifully restored property offering a peaceful stay steeped in centuries of...
7 nights from £766 *
British Travel Awards 2025
Best company for UK holiday home rentals
7 nights from £2814 * booking fees included
Pen Den Har
61706 bedroom, dog friendly home with sea views in Kingsand, Cornwall.
Come and fall under the spell of this very special house, perfectly positioned in the heart of the utterly charming villages of Kingsand and Cawsand. Set in a plum elevated positio...
7 nights from £2814 *
7 nights from £872 booking fees included
Marina View
61533 bedroom apartment with sea views in Falmouth, South Cornwall.
A stunning, elegant waterside apartment in the heart of the marina in Falmouth overlooking bobbing boats within a gated development. A wonderful location for exploring the town on ...
7 nights from £872
7 nights from £1512 booking fees included
The Bowjy
61724 bedroom, dog friendly holiday cottage near Looe, South Cornwall.
Come and create cherished holiday memories with family and friends at this stunning barn conversion. Tucked away along a quiet country lane, it is ideally located within easy reach...
7 nights from £1512
7 nights from £924 * booking fees included
Larkspur Cottage
61513 bedroom, dog friendly cottage near the beach in Praa Sands.
Located in the peaceful village of Germoe in west Cornwall, Larkspur Cottage is a picture-perfect thatched home brimming with history, charm and countryside tranquility. This encha...
7 nights from £924 *
7 nights from £1040 booking fees included
Horizons
61773 bedroom cottage with sea views in Praa Sands, West Cornwall.
Horizons is a stunning coastal home set back from the sandy beach and turquoise sea at beautiful Praa Sands, one of Cornwall’s most loved beach destinations. Sleeping six guest...
7 nights from £1040
7 nights from £546 booking fees included
The Grove
60892 bedroom, dog friendly cottage near Mevagissey, South Cornwall.
Nestled in a peaceful nook of the Cornish countryside you will find this charming traditional cottage with both the north and south coast only a 20 minute drive away. This tranquil...
7 nights from £546
We are Gold accredited with the Green Tourism Business Scheme.
Green Tourism Business Scheme
As a company, we look across our business and try to make sustainable changes and decisions. From using recycled paper in our printers to putting in measures for using less energy in our offices, we keep an eye on our impact on the environment.
Beyond our offices, we have passed on the same ethics to our holiday cottage owners by setting up our own Green Scheme that they can join. Each property has to tick off a certain number of actions to be included in the scheme, many of which go above and beyond the GTBS requirements.
A month of transition and promise, October sees summer bid its final farewell and autumn gracefully take the stage. All around the county, trees shed their lush sheaths and hues of burnt orange, rust and deep red leak across the landscape. With children finishing their first half term of the new school year and work routines heavy following summer's games, why not take the opportunity to recoup and catch up together? At Classic Cottages we have a wide range of self-catering cottages offering a luxury base from which to enjoy Cornwall's autumnal tones. Tread leaves, play on empty beaches and enjoy whatever comes your way, an October half term holiday in Cornwall is not one to be missed. Find your favourite cottage today and take a step closer to your next adventure together.
