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Shaftesbury

Shaftesbury’s elevated position provides wonderful views over three counties, this was once a medieval trading post; today the town offers a lovely picturesque location for a cottage holiday in Dorset.

There are centuries of fascinating history here, independent shops and regular weekly markets and a monthly farmers market. For a glimpse of old England visit Gold Hill with its chocolate box thatched cottages and ancient cobblestones, familiar to thousands as the location for the fondly remembered ‘Hovis’ advert.

Close by there are lots of places to visit and things to do; Shaftesbury Arts Centre puts on a year-round program of plays, films, workshops and exhibitions. Sherbourne Castle dates back to 1594 and was built by Sir Walter Raleigh. This historic house displays 400 years of history and has fascinating interiors and marvellous collections furniture, art and porcelain. Outside is no less impressive with stunning architecture and acres of grounds designed by ‘Capability Brown’.

Shaftesbury is located amongst beautiful tranquil countryside just made for relaxing outdoor activities. The Wessex Ridgeway Trail passes through the heart of the Dorset countryside and due to its ridge-top elevation provides wonderful views. Also close by are numerous excellent cycling routes where you can get out and about and if you don’t bring your own, bicycle hire is available locally.

Other activities within the vicinity include a number of riding stables offering lessons and cross country rides and coarse fishing at Todber Manor Fisheries.

To discover this beautiful corner of Dorset, please take a look at our selection of Cottages in Sherbourne and surrounding area.
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  • Motcombe, near Gillingham, Dorset
    Motcombe, near Gillingham, Dorset×

    Bankside and Lakeside Hut - Lakeside Hut

    Motcombe, near Gillingham, Dorset

    2
    1
    1
    2
    Ref: W43465
    Key Features:
    - Car parking on site - Pets go free - Detached Property - Rural Location
    Enjoy on-site fishing or exploring the many local attractions from this peaceful retreat. Close to Shaftesbury.
    Prices from
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    Pets included
    Pets go free

    Accommodation at

    These wonderful shepherd’s huts are located on the edge of a carp lake, and are now delightful holiday cabins, situated in the grounds of the owner’s home, offering a peaceful retreat on the edge of the Dorset, Somerset and Wiltshire border. Watch the continuous antics of the varied birdlife visiting the lake from the balcony. Set in the heart of the Blackmore Vale, renowned for its natural beauty, Bankside and Lakeside Hut provide an ideal base from which to explore the...

  • Fifehead Magdalen, near Gillingham, Dorset
    Fifehead Magdalen, near Gillingham, Dorset×
    Newly Listed
    The Byre

    The Byre

    Fifehead Magdalen, near Gillingham, Dorset

    2
    1
    1
    1
    Ref: UKC2279
    Key Features:
    - Wifi - Car parking on site - Pets go free - Detached Property - Garden / Patio - Ground Floor Facilities - Rural Location - Woodburning Stove
    The Byre offers a great holiday retreat for couples with a small child to get away from it all and enjoy a superb part of Dorset.
    Prices from
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    Pets included
    Pets go free

    Accommodation at

    In a lovely location in the quiet village of Fifehead Magdalen between Shaftesbury, Gillingham and the abbey town of Sherborne, this detached cottage in Hamstone is set in the grounds of the owners’ Grade II listed home and has splendid views over Duncliffe Wood, Melbury Beacon and the Blackmore Vale. Shaftesbury with its famous Gold Hill and character shops and Sherborne with its abbeys, castle and restaurants are delightful places to visit. There are many attractions within...

  • Semley, Shaftesbury, Dorset
    Semley, Shaftesbury, Dorset×
    2
    1
    1
    2
    Ref: B4337
    Key Features:
    - Wifi - Car parking on site - Pub within 1 mile - Garden / Patio - Ground Floor Facilities - Rural Location
    Close to cycle paths and marked footpaths as well as historic houses and monuments such as Stonehenge.
    Prices from
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    Pets included
    Pets go free

    Accommodation at

    In an Area of Outstanding Natural Beauty

    Excellent walking and cycling area

    Set in a peaceful rural location on the borders of Dorset and Wiltshire, Whitebridge Farm (refs B4337 and B6844), is not a working farm but is ideal for a family touring holiday with excellent walking and cycling in an Area of Outstanding Natural Beauty. Both the South Wiltshire and Dorset cycle ways pass nearby and there are numerous waymarked walks, including the half-hour Shaftesbury town...

    Whitebridge Farm Holiday Cottages - Pond Cottage
    6
    3
    3
  • Compton Abbas, near Shaftesbury, Dorset
    Compton Abbas, near Shaftesbury, Dorset×

    Nut Bush

    Compton Abbas, near Shaftesbury, Dorset

    2
    1
    1
    2
    Ref: W8523
    Key Features:
    - Car parking on site - Pub within 1 mile - Pets go free - Garden / Patio
    In a rural location, Nut Bush boasts beautiful countryside views where wildlife can be spotted! There are also some great footpaths nearby.
    Prices from
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    Pets included
    Pets go free

    Accommodation at

    Superb country views

    Nestling in a rural location, down a little country lane surrounded by glorious unspoilt downland, is this cosy furnished bungalow. Adjoining the owner’s property, there are superb country views from the bungalow overlooking fields, which abound in wildlife, with deer, foxes, badgers and rabbits often passing by. Nearby there are ample footpaths across Fontmell Down, an area steeped in ancient history. A short drive takes you to Compton Abbas Airfield,...

  • Motcombe, near Gillingham, Dorset
    Motcombe, near Gillingham, Dorset×

    Bankside and Lakeside Hut - Bankside

    Motcombe, near Gillingham, Dorset

    2
    1
    1
    3
    Ref: UKC1414
    Key Features:
    - Car parking on site - Pub within 1 mile - Pets go free - Rural Location
    This shepherd’s hut provides idyllic lakeside accommodation, for couples looking to relax, or explore this isolated and rural location.
    Prices from
    0
    Pets included
    Pets go free

    Accommodation at

    These wonderful shepherd’s huts are located on the edge of a carp lake, and are now delightful holiday cabins, situated in the grounds of the owner’s home, offering a peaceful retreat on the edge of the Dorset, Somerset and Wiltshire border. Watch the continuous antics of the varied birdlife visiting the lake from the balcony. Set in the heart of the Blackmore Vale, renowned for its natural beauty, Bankside and Lakeside Hut provide an ideal base from which to explore the...

    Bankside and Lakeside Hut - Lakeside Hut
    2
    1
    1
  • Sandley, near Gillingham, Dorset
    Sandley, near Gillingham, Dorset×

    Green Oak Cottage

    Sandley, near Gillingham, Dorset

    4
    2
    2
    1
    Ref: W43695
    Key Features:
    - Wifi - Car parking on site - Pub within 1 mile - Pets go free - Garden / Patio - Rural Location
    A holiday cottage set in a rural location with a patio area that has some stunning views of the countryside.
    Prices from
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    Pets included
    Pets go free

    Accommodation at


    This holiday cottage, with an outbuilding between the two properties, has a large, private and secluded patio area perched above the fields behind, offering far-reaching rural views across Blackmore Vale and cider orchards. There is a raised pond and fountain where you can listen to the sounds of birdsong. Locally produced award-winning cider is available from the farm opposite. The interior has been decorated and furnished, with great attention to detail and style. Attached to...

  • East Orchard, near Shaftesbury, Dorset
    East Orchard, near Shaftesbury, Dorset×

    Bowling Green Farm - Tarrant Cottage

    East Orchard, near Shaftesbury, Dorset

    4
    2
    1
    2
    Ref: 14557
    Key Features:
    - Car parking on site - Pub within 1 mile - Garden / Patio - Ground Floor Facilities - Rural Location
    All on the ground floor and adapted for assisted wheelchair users this cottage is in the heart of the Blackdown Vale.
    Prices from
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    Pets included
    Pets go free

    Accommodation at

    Situated in a courtyard of similar properties, these comfortable cottages are adjacent to the owners home and 8 acres of land, in the heart of the Blackdown Vale, an AONB, where the countryside is alive with deer, buzzards and pheasants, and just 4 miles south of Shaftesbury, where the famous Gold Hill is located. Nearby there is golf, gymnasium, fishing, 1 mile, and cycle paths and walking. Within easy driving, the historic towns of Blandford and Salisbury. Visit Longleat House and...

    Bowling Green Farm - Marlott
    4
    2
    2
  • Kington Magna, near Gillingham, Dorset
    Kington Magna, near Gillingham, Dorset×

    Vale View

    Kington Magna, near Gillingham, Dorset

    4
    2
    2
    1
    Ref: 26274
    Key Features:
    - Wifi - Car parking on site - Detached Property - Garden / Patio - Rural Location
    Providing upside-down accommodation this cottage is ideally located for visiting Longleat Safari Park, Weymouth and even the city of Bath.
    Prices from
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    Pets included
    Pets go free

    Accommodation at

    In delightful north Dorset between Shaftesbury, 7 miles, and Sherborne, 9 miles, and set in the owner’s grounds, this well presented cottage for 4 is ideally located to explore the many attractions nearby. Enjoy Stourhead House and Gardens, Longleat House and Safari Park, Yeovilton Fleet Air Arm Museum and many historic houses. Spend days out at Weymouth and Poole on the south coast or inland at the Georgian city of Bath with museums, Roman Baths, Pump Room and shops. Shop, pub...

  • Wyke, near Gillingham, Dorset
    Wyke, near Gillingham, Dorset×

    Cherry Orchard Cottages - Barn Owl Cottage

    Wyke, near Gillingham, Dorset

    4
    2
    2
    2
    Ref: 27737
    Key Features:
    - Car parking on site - Pub within 1 mile - Detached Property - Garden / Patio - Rural Location
    Children will love Longleat Safari Park and there are beaches galore along the World Heritage Jurassic Coast.
    Prices from
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    Pets included
    Pets go free

    Accommodation at

    Situated on the edge of Gillingham in North Dorset, close to the Wiltshire/Somerset border, these two detached converted barns (refs 27736 and 27737), both for four and which can be booked independently or together, offer very presentable quality holiday accommodation in which to unwind, relax and enjoy the wealth of countryside and many attractions to be found in Dorset, Somerset and Wiltshire. Within easy driving distance are family attractions such as the Yeovilton Fleet Air Arm...

    Cherry Orchard Cottages - The Old Cattle Stall
    4
    2
    2
  • Shaftesbury, Dorset
    Shaftesbury, Dorset×

    Rosina

    Shaftesbury, Dorset

    4
    2
    2
    0
    Ref: 27455
    Key Features:
    - Wifi - Enclosed Garden / Patio - Pub within 1 mile
    Super family accommodation within walking distance of the town centre and an easy drive to attractions.
    Prices from
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    Pets included
    Pets go free

    Accommodation at

    This cosy, 300-year old, semi-detached cottage for 4 is situated in Enmore Green, within walking distance of the historic town centre of Shaftesbury. Ideally placed for exploring the popular and beautiful Blackmore Vale, guests can enjoy wonderful country walking with fantastic views up on Gold Hill. There is much to visit within easy driving distance of this holiday property, including Stourhead House and Gardens, Salisbury Cathedral and Longleat House and Safari Park. Shop ½...

  • Sturminster Newton, Dorset
    Sturminster Newton, Dorset×

    The Kite

    Sturminster Newton, Dorset

    4
    2
    2
    0
    Ref: E4133
    Key Features:
    - Wifi - Car parking on site - Enclosed Garden / Patio - Pub within 1 mile - Garden / Patio - Rural Location - Woodburning Stove
    In beautiful open countryside, and boasting its own small garden, this spacious, converted and tastefully decorated holiday cottage is one of three set midway between Blandford Forum, 10 miles, and Shaftesbury
    Prices from
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    Pets included
    Pets go free

    Accommodation at

    In beautiful open countryside, and boasting its own small garden, this spacious, converted and tastefully decorated holiday cottage is one of three set midway between Blandford Forum, 10 miles, and Shaftesbury. Many National Trust properties – including Stourhead House and Gardens, Haynes Motor Museum, the Fleet Air Arm Museum at Yeovilton, Monkey World, Longleat Safari Park and the Jurassic Coast are easily accessible. Golf, fine walking, fishing and riding nearby. Kite cottage is a...

  • Gillingham, near Shaftesbury, Dorset
    Gillingham, near Shaftesbury, Dorset×

    D’Urbervilles

    Gillingham, near Shaftesbury, Dorset

    4
    2
    1
    2
    Ref: 30002
    Key Features:
    - Wifi - Car parking on site - Enclosed Garden / Patio - Pub within 1 mile - Pets go free - Detached Property - Garden / Patio - Ground Floor Facilities
    This single storey holiday property is ideal for discovering the delights of Dorset, Somerset and Wiltshire.
    Prices from
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    Pets included
    Pets go free

    Accommodation at


    In Gillingham, north Dorset, near the Somerset and Wiltshire border between the abbey town of Sherborne and the Saxon town of Shaftesbury, with its famous Gold Hill, this detached single storey holiday home for 4 offers a great location to explore this popular area. Many family attractions within easy driving include Longleat House and Safari Park, Stourhead House and Gardens, Yeovilton Fleet Air Arm Museum, Haynes Motor Museum and Montacute House to name a few. Poole,...

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