Tolpuddle Cottages
Between Dorchester and Poole, deep in Dorset's hilly countryside, Tolpuddle is a picture postcard village of thatched cottages, leafy lanes and a pretty church. The village is famous for its Tolpuddle Martyrs, a group of agricultural workers who attempted to form the first ever trade union but whose efforts resulted in their deportation to Australia as criminals. A museum in the village now tells the tale through a series of fascinating exhibits.
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.We have 6 self catering cottages in Tolpuddle to show you...
7 nights from £605 * booking fees included
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 £605 *
7 nights from £573 * booking fees included
Beehive Cottage
40732 bedroom thatched, dog friendly cottage near Dorchester, Dorset.
Beehive Cottage is a charming and cosy cottage, on a quiet lane opposite St Mary's church in the village of Puddletown. Surrounded by farmland, the pretty village is nestled in the...
7 nights from £573 *
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20% off
14 Aug 2026 - 21 Aug 2026
From £788.40 £643.32 booking fees included
We’ve been raising the standards of self catering holidays since 1977.
Our family ethos
Tony and Clare Tregoning started the business back in 1977 and their dedication to quality and excellence is at the heart of everything we do. Tony is sadly no longer with us, but we still adhere to their original ethos of finding holiday homes we would like to stay in and have slowly grown the company to find the best picks of properties across the counties. Plus Clare still drops in to keep us on our toes.
As an independent, family-run company, we wouldn’t expect you to stay anywhere we wouldn’t want to stay ourselves. And we’re pretty picky. We want you to walk into your handpicked holiday home and say ‘wow’, sit back and relax.
7 nights from £569 * booking fees included
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 £569 *
7 nights from £793 booking fees included
Halcyon Cottage
46932 bedroom cottage close to the beach, Lulworth Cove and Dorchester, Dorset.
Less than one mile from Lulworth Cove, part of the only World Heritage Site in England, Halcyon Cottage is a pretty, detached stone cottage in the heart of the village of West Lulw...
7 nights from £793
British Travel Awards 2025
Best company for UK holiday home rentals
7 nights from £640 * booking fees included
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 £640 *
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35% off
14 Aug 2026 - 21 Aug 2026
From £2063.00 £1363.00 booking fees included
From £298 per night + £63 booking fees
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...
From £298 per night
Show properties within 20 miles of Tolpuddle
