46 self-catering cottages for October half term in Dorset
7 nights from £802
2 Penny’s Cottages
25313 bedroom house in the historic village of Corfe Castle, Dorset.
Set in the historic village of Corfe Castle, 2 Penny's Cottages is a semi-detached family house that welcomes all its visitors, it is a real home-from-home. The property has been b...
7 nights from £802
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50% off
17 May 2026 - 22 May 2026
From £900.00 £450.00
7 nights from £420
The Old School Gables
24902 bedroom cottage near the market town of 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 extrem...
7 nights from £420
7 nights from £696
Hatts Barn
20932 bedroom, rural holiday cottage near Shaftesbury, Dorset.
Hatts Farm is a working farm located in a National Landscape. The farm spreads over 150 acres, located in the stunning countryside of the Dorset and Wiltshire border. Hatts Barn...
7 nights from £696
7 nights from £900
Barbridge Cottage
18052 bedroom, rural holiday cottage near Bridport, Dorset.
Heading up the short, unmade track you will find the idyllic setting for the cottage. You enter into a wonderful, vaulted living space, flooded with the light and a cosy wood burne...
7 nights from £900
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25% off
23 May 2026 - 30 May 2026
From £1100.00 £825.00
7 nights from £510 *
The Old Coach House
13862 bedroom, dog friendly cottage near the county town of Dorchester, Dorset.
This pretty detached former coach house can be found in the rural Dorset countryside, within easy reach of the stunning coastlines of the Jurassic Coast, a World Heritage Site. ...
7 nights from £510 *
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20% off
15 May 2026 - 22 May 2026
From £680.40 £544.32
7 nights from £870
Sunnyholme
14604 bedroom house near the beach in Studland, Dorset.
The Isle of Purbeck is a stunning National Landscape between Poole and Swanage, boasting one of the most spectacular coastlines in Dorset. Sunnyholme is an extremely spacious de...
7 nights from £870
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.
