Self catering holiday cottages in Shaftesbury, Dorset, England

holiday in ShaftesburyShaftesbury is an historic market town with breathtaking views of the surrounding Dorset countryside. The "Shaston" of Thomas Hardy's novels, Shaftesbury is one of the oldest and highest towns in England.


Advice on Cottage Holidays in Shaftesbury

Gold Hill is the most famous hill in Shaftesbury. With its worn polished cobbles, it's most recently famous for the Hovis Bread Advertisement back in the 1980's when the young boy struggled to push his bicycle up the steep hill.

Market day is Thursday, with a good Farmers Market on the first Saturday of every month.  Coffee shops and cafes abound, in particular pay a visit to Turnbull's Deli at the top of the High Street for great coffee, cakes and a huge selection of cheese.

Book a Shaftesbury cottage and look forward to discovering some of the best of Dorset on holiday.

23 rental properties

Ryecross Rural Retreat near Shaftesbury, Shaftesbury, Dorset, West Country, England

2 bedroom Farm Cottage

sleeps 2 - 4 guests
2 - 4
2 bedrooms
2
1 bathrooms
1
no dogs allowed
3 star

Get away from it all with a stay at this idyllic rural retreat near the attractive hillside town of Shaftesbury in Dorset.

Weekly Price from: £276
Next availability:
from 22 July to 22 August 20 from 31 August to 07 September 20

The Beams Country Cottage, East knoyle, Wiltshire, West Country, England

1 bedroom Couple's Rural Retreat, Shaftesbury 4 miles away

sleeps 1 - 2 guests
1 - 2
1 bedrooms
1
1 bathrooms
1
dog-friendly cottage, 1 dog(s) welcome
1
4 star

Whisk the one you love away for a romantic break at this idyllic English country cottage nestled close to the village of East Knoyle in Wiltshire, with access to an outdoor heated swimming pool in season and great walks nearby, this is a fantastic rural retreat for just two.

Special features: free internet access, pool ().

Weekly Price from: £250
Next availability:
from 04 August to 11 August 20 from 26 August to 05 September 20

The Old Chapel Conversion, Huntingford, Dorset, West Country, England

1 bedroom Chapel Conversion, Shaftesbury 6 miles away

sleeps 1 - 4 guests
1 - 4
1 bedrooms
1
1 bathrooms
1
no dogs allowed
5 star

For a self-catering holiday for 2 out of the ordinary in Dorset, stay in a unique one bedroom converted chapel with twin beds high up in the eaves on the gallery overlooking the cosy living area below; during your stay discover the pretty countryside on the Dorset Wiltshire borders, the National Trust property of Stourhead House, Wincanton for racing and Longleat Safari Park.

Weekly Price from: £269
Next availability:
from 29 July to 14 August 20 from 21 August to 04 September 20

Chaffeymoor Grange, Gillingham, Dorset, West Country, England

10 bedroom Mansion, Shaftesbury 8 miles away

sleeps 8 - 24 guests
8 - 24
10 bedrooms
10
9 bathrooms
9
dog-friendly cottage, 2 dog(s) welcome
2

Wonderful 10 bedroom manor house in the Blackmoor Vale surrounded by beautiful gardens and lush Dorset countryside.

Special features: free internet access, tennis court, games room.

Weekly Price from: £5800


Special Offer: from 12 July to 31 August 20
Late availability: from 12 July to 22 July 20

The Old Stables Holiday Barn, Winterborne Stickland, Dorset, West Country, England

3 bedroom Barn Conversion, Shaftesbury 10 miles away

sleeps 3 - 6 guests
3 - 6
3 bedrooms
3
2 bathrooms
2
dog-friendly cottage
5 star

Family-friendly and dog-friendly barn conversion with modern interior, situated within a small development on a working farm, ideal for rural retreat breaks and within reach of the Jurassic Coast.

Special features: free internet access, games room.

Weekly Price from: £360
Next availability:
from 14 July to 17 July 20 from 30 October to 04 December 20

Whitey Top Lodge, Sixpenny Handley, Dorset, West Country, England

2 bedroom Farmstay Lodge, Shaftesbury 10 miles away

sleeps 2 - 4 guests
2 - 4
2 bedrooms
2
1 bathrooms
1
no dogs allowed
4 star

Modern stylish 2 bedroom holiday lodge with warm bubbly outdoor private hot tub in a rural setting on a dairy farm, within around 30 minutes' drive of Salisbury and the New Forest National Park.

Special features: free internet access, outdoor hot tub.

Weekly Price from: £520
Next availability:
from 30 October to 31 October 20 from 13 November to 07 May 21

Apple Tree Cottage, Blandford Forum, Dorset, West Country, England

5 bedroom Thatched Cottage, Shaftesbury 10 miles away

sleeps 6 - 10 guests
6 - 10
5 bedrooms
5
3 bathrooms
3
no dogs allowed
5 star

Pretty 5 bedroom thatched country cottage, near Blandford Forum, with warm bubbly outdoor hot tub in garden.

Special features: free internet access, outdoor hot tub.

Weekly Price from: £897
Next availability:
from 13 July to 14 July 20 from 30 August to 04 September 20

Corner Pet-Friendly Barn, Dorset AONB, Winterborne Stickland, Dorset, West Country, England

2 bedroom Barn Conversion, Shaftesbury 11 miles away

sleeps 1 - 4 guests
1 - 4
2 bedrooms
2
2 bathrooms
2
dog-friendly cottage, 2 dog(s) welcome
2
5 star

This 2 bedroom pet-friendly barn conversion is located within a development of six holiday barns in a tranquil rural setting close to the Purbeck Heritage Coast and the Jurassic Coast, shared facilities on site include a games room with pool table, table football and air hockey, whether for a family holiday or a getaway with friends, there is plenty to keep you entertained here.

Special features: free internet access, games room.

Weekly Price from: £348
Next availability:
from 14 August to 21 August 20 from 25 September to 24 December 20

The Victorian Barn Self Catering Holidays with Pool & Hot Tubs, Dorset., Blandford Forum, Dorset, West Country, England

32 bedroom Cottage Complex, Shaftesbury 11 miles away

sleeps 4 - 70 guests
4 - 70
32 bedrooms
32
 32 bathrooms
32
no dogs allowed
4 star

Luxurious barn conversion accommodation, sleeping up to 14 people in style and comfort, with lots to offer including access to excellent leisure facilities on site including an indoor heated swimming pool, a sauna, hot tub and a gym, as well as a games room with full-size pool table, a quiz machine and football table and an outdoor play area for children, as well as coarse fishing lakes.

Special features: free internet access, pool (Please enquire with your guest numbers so we can direct you to the perfect property!), games room, outdoor hot tub, sauna, Gold Award Winning Cottage.

Weekly Price from: £300


Special Offer: from 12 July to 28 December 20
Late availability: from 12 July to 04 September 20

Little Cheriton House, South Cheriton, Somerset, West Country, England

7 bedroom Large Country House, Shaftesbury 12 miles away

sleeps 16 - 18 guests
16 - 18
7 bedrooms
7
5 bathrooms
5
no dogs allowed

Stylish and impressive 7 bedroom manor house with stunning country views, private outdoor hot tub and spacious elegant accommodation, half an hour's drive from Yeovil.

Special features: free internet access, outdoor hot tub.

Weekly Price from: £3200
Next availability:
from 17 July to 24 July 20 from 27 July to 31 July 20

Shepherd's Hut Barn, rural Dorset, Winterborne Whitechurch, Dorset, West Country, England

3 bedroom Holiday Barn, Shaftesbury 15 miles away

sleeps 2 - 6 guests
2 - 6
3 bedrooms
3
2 bathrooms
2
dog-friendly cottage, 2 dog(s) welcome
2
5 star

Want to stay somewhere with tranquil rural views over fields and pastures where you can relax and unwind in Dorset? This 3 bedroom family-friendly and dog-friendly ban could be perfect, close to Thomas Hardy's Country and within reach of Dorset's Jurassic Coast for day trips.

Weekly Price from: £394
Next availability:
from 07 August to 10 August 20 from 13 August to 14 August 20

Quaker Dogs-welcome Cottage, South West England , Sherborne, Dorset, West Country, England

2 bedroom Cottage, Shaftesbury 15 miles away

sleeps 1 - 4 guests
1 - 4
2 bedrooms
2
1 bathrooms
1
dog-friendly cottage, 1 dog(s) welcome
1
4 star

Charming stone-built pet-friendly cottage with 2 bedrooms located in Sherborne, on days out from this Dorset location visit Shaftesbury, the city of Salisbury with its wealth of historical buildings or Bath with its impressive Roman spa.

Weekly Price from: £268
Next availability:
from 13 July to 01 October 20