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 38 cottages in Dorset this October
7 nights from £395
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 Owners' home, (who may not be resident...
7 nights from £395
7 nights from £397
The Linhay
26611 bedroom, rural cottage near the beach near Bridport, Dorset.
The Linhay is a tucked away single-storey retreat – an ideal base for exploring the wonderful coastline. The cottage nestles alongside the barns, with a fully enclosed gravel court...
7 nights from £397
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 £397
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 windows to its own enclosed outside space – t...
7 nights from £397
7 nights from £400
Owl's Nest Cottage
29421 bedroom, dog friendly self catering cottage near Sherborne, Dorset.
This cosy, compact, delightful bolthole for two is set in a wonderfully tranquil hamlet in north Dorset with village shops and a choice of two pubs within two miles. Built in lo...
7 nights from £400
7 nights from £407
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 £407
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35% off
28 Jun 2019 - 5 Jul 2019
£535.59 £348.40
7 nights from £436
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 £436
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15% off
19 Jul 2019 - 23 Jul 2019
£550.50 £467.93
7 nights from £452
Lottie’s Loft
25651 bedroom, rural holiday cottage near Beaminster, Dorset.
Lottie’s Loft is a luxurious first floor barn conversion, a gorgeous bolthole surrounded by beautiful Dorset countryside. Exterior steps lead from the decking to a balcony with bes...
7 nights from £452
7 nights from £561 *
Tolpuddle Cottage
37523 bedroom thatched, dog friendly cottage in Tolpuddle, Dorset.
This pretty thatched cottage is in the tranquil historic village of Tolpuddle, just 15 miles from the World Heritage Jurassic Coast. An ideal base for a family holiday or perfect f...
7 nights from £561 *
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10% off
5 Jul 2019 - 12 Jul 2019
£1109.49 £998.54
Arrive at your handpicked holiday home safe in the knowledge it’s been fully inspected.
Quality inspections
We check our holiday homes to ensure that everything is up to our high standards for your holiday, from provision of our above standard minimum inventory to how fluffy the towels are, we make sure you’ll have a comfortable stay.
Hardworking teams of housekeepers will have the place spick and span, ready for your arrival, so when you get there you can just relax.
7 nights from £561
The Chalet on the Beach
3351Beach Chalet 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 £561
7 nights from £409
The Old School Gables
24902 bedroom dog friendly holiday cottage near Bridport, Dorset.
The pretty Dorset village of Drimpton is set in lovely countryside a short drive inland from the stunning Jurassic Coast. This original school house has been converted into extreme...
7 nights from £409