Holiday Homes in Shaftesbury, Dorset

Self-Catering Holiday Cottages in Shaftesbury

Shaftesbury, set near the Cranborne Chase Area of Outstanding Natural Beauty, is an ideal destination for a self-catering escape. Renowned for its iconic Gold Hill, made famous in the 'Hovis bread' advert, this Dorset town offers remarkable historic cottages and stunning views of the countryside. Situated in Thomas Hardy country, Shaftesbury is one of England’s oldest and highest towns. With its quaint shops, cozy cafes, and rustic country inns, visitors can also enjoy a vibrant farmer’s market on select days. Shaftesbury is a delightfully charming choice for a self-catering holiday in the West Country.

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Booking your holiday accommodation in Shaftesbury early is recommended for the best choice of holiday rentals.

Viewed 10× this week No booking fee

Waterlake Cottage, Orcheston, nr Stonehenge

Stonehenge, Wiltshire ~19 miles from Shaftesbury

Sleeps 2–4 2 Bedrooms 🚫 No Dogs

Next Available 21/03 to 26/03/2026

Facilities

Type of Holiday

Weekly from £650 – £650

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Viewed 15× this week

Little Cheriton House

South Cheriton, Somerset ~11 miles from Shaftesbury

Sleeps 7–18 7 Bedrooms 🐾 1 Dog

Next Available 23/03 to 27/03/2026

Facilities

Type of Holiday

Weekly from £3,000 – £6,620

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Viewed 20× this week

Portman House

Pylle, Somerset ~19 miles from Shaftesbury

Sleeps 8–16 8 Bedrooms 🐾 2 Dogs

Next Available 23/03 to 27/03/2026

Facilities

Type of Holiday

Weekly from £4,175 – £7,480

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Viewed 17× this week

Apple Cottage Hot Tub Retreat

Pylle, Somerset ~18 miles from Shaftesbury

Sleeps 1–4 2 Bedrooms 🐾 2 Dogs

Next Available 26/03 to 02/04/2026

Facilities

Type of Holiday

Weekly from £740 – £1,600

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Viewed 24× this week

Lower Hedge Farm

Shepton Mallet, Somerset ~18 miles from Shaftesbury

Sleeps 5–12 5 Bedrooms 🐾 2 Dogs

Next Available 23/03 to 27/03/2026

Facilities

Type of Holiday

Weekly from £2,500 – £4,425

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Cottages, Apartments & Lodges in Shaftesbury, Dorset, England

RuralHomeStays.Com features holiday home(s) within or close to Shaftesbury, enjoy browsing through the available options. We hope you find the perfect holiday house for you in Shaftesbury, Dorset.

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Cottage Breaks in Shaftesbury: A Charming Dorset Town

Sitting just outside of the Cranborne Chase Area of Outstanding Natural Beauty, Shaftesbury is a charming Dorset town in which to take a self-catering break.

What Does Shaftesbury Offer for Cottage Holidays in Dorset?

Perhaps best known for having featured in the 'Hovis bread' advert, Shaftesbury is home to glorious Gold Hill where there are some wonderful historic cottages and fabulous views over the surrounding Dorset countryside. This is Thomas Hardy country, and the charming market town of Shaftesbury is said to be one of England's oldest and highest-placed towns. With a good choice of shops, cafes, and country inns, as well as a farmer's market on certain dates, Shaftesbury is a superbly charming place for a vacation in the West Country.

Updated 17 November 2025