One of many pretty cottages in the small villages and hamlets surrounding Dorchester.

Find My Favourite Holiday Cottages in Dorchester

A beautiful historic town in the county of Dorset and home town of the writer Thomas Hardy, Dorchester overflows with interesting architecture and other sights for visitors to Dorset’s County Town to enjoy. The clock tower and church hold particular interest because of their quirky but equally stunning design and construction. Be sure also to pay homage to the statue of Thomas Hardy at the top of the town.

Lose yourself as you wander around the town, discovering its historic buildings. Indulge in the French market that you won’t find anywhere else nearby this side of the Channel. Wander around the beautiful Borough Gardens, which includes two tennis courts, a beautiful bandstand and a clock tower – the atmosphere of the blossoming flower beds and the frequent live music playing is so inviting and welcoming that you could spend a long summer day relaxing here.

A partially thatched Dorset cottage overlooks a large and secure lawned garden.
Sleeps
4
Bedrooms
3

Enjoy the unspoilt beauty of the hamlet of Benville, Dorset, just as Thomas Hardy described it a century ago, with a stay at Benville Cottage, a historic child-friendly cottage with three bedrooms, a large garden with three terraced lawn areas, an Inglenook fireplace, and 17th-century stone wall carving.

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A stone barn stands alone surrounded by wheat fields.
Sleeps
6
Bedrooms
3

Blagdon Lower Barn promises true seclusion in its beautifully positioned remote location amid the Dorset countryside. Fields surround the pet-friendly cottage near Dorchester. It boasts extensive gardens with rural views and an interior with a high brick arch, open fire, open-plan design and luxurious décor.

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Large, thatched Dorset Farmhouse overlooking a courtyard.
Sleeps
8
Bedrooms
4

Manor Farmhouse is a thatched and beautifully presented country cottage near Maiden Newton, sleeping eight in four bedrooms with expansive rural views and river frontage, situated in a peaceful and idyllic location.

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Gable end of a stone-built Dorset holiday cottage overlooking a shrub-filled front garden.
Sleeps
5
Bedrooms
3

Discover The Old School House for unforgettable self-catering holidays in Dorset. This converted Victorian school in Piddletrenthide seamlessly blends historic charm with modern comfort. Relax by the wood-burning stove, enjoy a reading room, and savour meals in the bright kitchen/diner. Three well-presented bedrooms include an en-suite double, a twin, and a skylit single. The family bathroom boasts a bath and a separate shower. Charming gardens and proximity to Dorchester and the Jurassic Coast make this pet-friendly cottage an ideal choice. Explore the full description for an enticing getaway.

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A 3-storey, brick-built, Dorset Mill House overlooks a cobbled courtyard.
Sleeps
12
Bedrooms
6

Mill House is a large Dorset holiday home in Maiden Newton, Dorset, which makes an ideal holiday retreat for large families and groups of friends, a Grade II listed child-friendly cottage featuring stylish décor, a games room, six spacious bedrooms, and a large enclosed garden with patio and barbecue.

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Other places of interest and well worth a visit are the Roman Town House in the grounds of the County Hall, which can be combined with the Durnovaria Town Walk, a town trail that follows the fortified boundary of the town in Roman times. Visit Maiden Castle and take a step back in time to the largest hill fort in England, extending 45 acres. It’s a beautiful ruin and well worth a look around.

From Dorchester, it’s only a short drive to the coast and the Regency resort of Weymouth with all its traditional seaside holiday attractions. There’s so much to experience in Dorchester that you’ll find yourself lost in its incredible history and culture.