Dorset Retreats for October Half Term
Watch summer fade into autumn from the comfort of a self-catering cottage in Dorset. We have a wide range of cottages peppered across Dorset of all different shapes and sizes available for an unforgettable autumn. Spend your days exploring Dorset from country to coast, treading golden leaves and breathing crisp air, and then when you're ready return to your home-from-home together. Read more
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.45 self-catering cottages for October half term in Dorset
7 nights from £1428
Oak Tree House
61124 bedroom, dog friendly holiday cottage near Dorchester, Dorset.
Oak Tree House is a particularly special property for gathering friends and family (plus the four-legged variety) together. Set in stunning grounds in the little village of Frampto...
7 nights from £1428
7 nights from £403
Kingfishers
60351 bedroom, dog friendly holiday cottage near Shaftesbury, Dorset.
Great care and attention has been put into this barn conversion, resulting in a truly cosy, yet spacious retreat for couples or solo travellers to enjoy. Located in Gillingham in n...
7 nights from £403
7 nights from £1138
Hood's
60452 bedroom, dog friendly self catering cottage near Bridport, Dorset.
**Hood's can accommodate flexible check in days – please contact us to request.** This stunning barn and milking parlour conversion is set within the glorious Dorset countryside...
7 nights from £1138
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25% off
10 Apr 2026 - 17 Apr 2026
£1400.00 £1050.00
7 nights from £412
Loaf At The Granary
60461 bedroom, dog friendly self catering cottage near Bridport, Dorset.
**Loaf At The Granary can accommodate flexible check in days – please contact us to request.** Loaf At The Granary is a gorgeous and sympathetic restoration of an ancient Dorset...
7 nights from £412
British Travel Awards 2025
Best company for UK holiday home rentals
Hood's and Loaf at Kingsland Farm
7 nights from £1550
7 nights from £750 *
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 £750 *
Whetley Farm
7 nights from £861
7 nights from £431 *
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 £431 *
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25% off
3 Apr 2026 - 10 Apr 2026
From £593.00 £444.75
7 nights from £431 *
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 £431 *
7 nights from £534 *
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 £534 *
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20% off
3 Apr 2026 - 10 Apr 2026
From £655.00 £524.00
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.
Country walks under rust-coloured canopies following forest trails of red, yellow and orange. Reviving strolls along the coast and empty beaches, waves on the shore sending a shower of salty kisses across your cheeks. Gentle afternoons spent in quiet towns, freed from merry crowds and content in the last of summer's glow. Dorset in October half term is a perfect retreat away from the ebb and flow of everyday life. Find a cottage amongst our portfolio and take your little ones by the hand. A holiday is just around the corner and memories ready to be made.
