October Breaks in Dorset
Great weather often hangs around until well into October in Dorset, so to celebrate the final flourishes of summer properly why not book a luxury self-catering cottage? Snugly one-bed retreat in a charming town, romantic hideaway with amazing sea views, or cottage in the country with space for all the gang, we'll help you pave the way to the holiday of your dreams this October. Read more
For a truly romantic getaway, browse through our list of cottages with hot tubs available this October. Spend your days exploring and soaking in the last of the summer rays, and then when you've had your fill return to your home-from-home and hop into a bubbling hot tub. Or how about a family-friendly cottage, perfect for little kids and big kids alike? October is a great time of year for families to make the most of all that Dorset has to offer with half term around the corner and lots of spook-tacular celebrations taking place ahead of Halloween. If you would like to revel in some peace and quiet, we have plenty of secluded cottages, offering lots of privacy and plenty of space for some quality R&R. At Classic Cottages, we pride ourselves on marketing the finest self-catering cottages around, handpicking and personally inspecting each one. Find your favourite today.
Pick from 28 cottages in Dorset this October
7 nights from £357
The Stables
19651 bedroom, rural holiday cottage near Dorchester, Dorset.
Dorset’s World Heritage Jurassic Coast is close to this comfortably furnished, single-storey, spacious cottage. Set within the grounds of the owner’s home, The Stables is self-cont...
7 nights from £357
7 nights from £363
The Linhay
26611 bedroom cottage near the beach near Bridport, Dorset.
The Linhay is a tucked away single-storey retreat – and an ideal base for exploring the wonderful coastline. The cottage nestles alongside the barns, with a fully enclosed gravel c...
7 nights from £363
Need more time? Reserve any cottage for up to 24 hours before booking.
24hr no commitment reservations
You can reserve your holiday dates on your favourite cottage for up to 24 hours. You might need to check with other guests in your party or simply consider whether this cottage is right for your holiday, either way we’re happy to give you the time to step away and mull over your options before paying a penny.
We’ll send you a reminder to see if you want it or not so you won’t lose out. Take time to think it over, you don’t have to rush your decision. Have a cup of tea and when you’re ready, hit the button to book your holiday and start looking forward to it.
7 nights from £363
The Dairy
26631 bedroom, rural cottage near the beach near Bridport, Dorset.
The Dairy is another extremely comfortable single-storey cottage in this small and friendly farm development. This property has French doors to its own enclosed outside space – the...
7 nights from £363
7 nights from £377
Badgers Cottage
30141 bedroom, dog friendly self catering cottage near Bridport, Dorset.
Badgers Cottage, a snug semi-detached cottage for two, is set in a farmyard, beautifully converted from an 18th Century stone barn. All on one level, the open plan design gives a w...
7 nights from £377
7 nights from £414
Pound Farm Cottage
40761 bedroom thatched self catering cottage near Sherborne, Dorset.
Pound Farm Cottage is a hidden gem; this listed thatched cottage has been thoughtfully renovated to create a spacious, stylish holiday home, retaining many of the original features...
7 nights from £414
7 nights from £486 *
Poacher's Cottage
45222 bedroom self catering cottage near Dorchester, Dorset.
Tucked away in the picturesque village of Buckland Newton, Poacher's Cottage is one of four gorgeous properties making up Dominey's Yard. Situated perfectly for exploring the beaut...
7 nights from £486 *
7 nights from £486 *
Gamekeeper's Cottage
45232 bedroom self catering cottage near Dorchester, Dorset.
Second in a row of pretty terraced cottages, this stylish property has been newly renovated to a very high standard. Gamekeeper's Cottage is one of four at Dominey's Yard, nestled ...
7 nights from £486 *
7 nights from £486 *
Woodcutter's Cottage
45242 bedroom self catering cottage near Dorchester, Dorset.
Rolling hills, bustling market towns, rich history and stunning beaches - have we persuaded you to holiday in Dorset yet? Finding a lovely cottage to stay in is the only thing you ...
7 nights from £486 *
Each and every one of our cottages is fully equipped with everything you’ll need on holiday.
Fully equipped cottages
All of our cottages have a standard list of equipment that goes above and beyond. As well as fluffy towels and readymade beds, our bare minimum includes everything you’ll need and more, from plenty of teaspoons to added extras such as gravy boats so no matter where you stay, you’ll be able to make your favourite home-cooked dishes.
Each inventory is regularly checked and counted so you won’t be stuck without a ladle and can leave your hairdryer at home, plus you’ll find a starter set of toiletries and cleaning products so you can get on with your holiday.
7 nights from £505
The Chalet on the Beach
3351Cabin on the beach sleeping two in Lyme Regis, Dorset.
Imagine a holiday right on the seashore of a very special beach, relaxing on your veranda with a glass of something refreshing, watching the gentle waves at one of the most famous ...
7 nights from £505
7 nights from £415
Wayside Cottage
44842 bedroom thatched, dog friendly cottage near Beaminster, Dorset.
A gorgeous, chocolate-box cottage that is the ideal escape, nestled in the heart of one of Dorset's picturesque villages. Just a stone's throw from the lovely local pub, Wayside Co...
7 nights from £415