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
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.Pick from 42 cottages in Dorset this October
7 nights from £754
The Lookout
57632 bedroom, dog friendly apartment with sea views, near Studland.
In an elevated position with views out to Swanage Bay, The Lookout is a modern, stylish, first floor apartment for up to four lucky guests and their four-legged friend to enjoy. Ta...
7 nights from £754
7 nights from £1035
Freshfields
57064 bedroom self catering cottage near Dorchester, Dorset.
Freshfields is a truly outstanding property in a picturesque Dorset village. Recently renovated throughout, the house provides space and privacy for all the family. Just a short dr...
7 nights from £1035
7 nights from £520
The Granary
56832 bedroom, dog friendly holiday cottage near Beaminster, Dorset.
Tucked away in a rural corner of west Dorset you will find The Granary; a single-storey cottage with a shared two acre woodland and wildflower meadow to while away holiday days in....
7 nights from £520
Whetley Farm
7 nights from £1040
7 nights from £520
The Dairy
56822 bedroom, dog friendly holiday cottage near Beaminster, Dorset.
A cosy single-storey cottage, a secret wood and wildflower meadow, all available to you in a location only a short drive of the World Heritage Jurassic Coast, are we tempting you y...
7 nights from £520
7 nights from £670
Bluebells
56242 bedroom, dog friendly cottage in walking distance of Bridport, Dorset.
Tucked away in a quiet location, yet just a stone's throw from bustling Bridport and the Jurassic Coast, you will find Bluebells. Situated at the end of a pretty row of cottages, t...
7 nights from £670
7 nights from £972
The Old Dairy
55512 bedroom, dog friendly cottage near Wimborne Minster, Dorset.
Situated within the southern neolithic ring of Knowlton Church and Earthworks and perfectly positioned under a Dark Sky Reserve, is The Old Dairy; a stylish and modern conversion t...
7 nights from £972
7 nights from £558
Pippins
53603 bedroom, dog friendly character cottage near Beaminster, Somerset.
Pippins is a picture postcard country cottage nestled in the charming Somerset village of North Perrott - not far from the Dorset border. This cosy home can cater for all of the fa...
7 nights from £558
We’re a Visit England Quality Accredited Agency for our high standards in holiday letting.
Quality Accredited Agency
Only the highest quality of accommodation is awarded Visit England accreditation. The assessment takes place over a few days and looks at all of our policies, practices and procedures, making sure we meet a five star standard for our guests.
We set our own standards above and beyond and we’re very proud of this accolade and all it represents.
7 nights from £1080
Seymour Barn
53142 bedroom, dog friendly barn conversion in Bridport, Dorset.
With the bustling market town of Bridport within striking distance, this beautiful barn conversion is the perfect home-away-from-home. A delightful spot to explore all the beauty a...
7 nights from £1080
7 nights from £888
Woodville Cottage
51513 bedroom, dog friendly home near the beach in Lyme Regis.
Woodville Cottage is a pretty and charming property, an annexe to a Grade II Listed Georgian building. Hidden away from the hustle and bustle of the elegant seaside town of Lyme Re...
7 nights from £888
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10% off
21 May 2025 - 28 May 2025
From £1173.00 £1055.70
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.
