30 Best Shaftesbury Estates on Holiday Lettings - Holiday cottages

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537 Vacation rentals

(14) Excellent 

Certificate of Excellence

22

Shaftesbury Vacation home rental

Dorset / Shaftesbury

3 5 2 nights min

  • 3 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Private garden
September Cottage is a mid 19th Century stone cottage situated in the lovely Dorset town of Shaftesbury. The cottage sleeps 5 and has been recently refurbished to a high standard, with stripped wooden floors throughout and consists of a living room, dining room, …see more

Certificate of Excellence

from $175 / night

$1,225 / week

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Responds fast!
avg. 2 hours 46 minutes

from $175 / night

(18) Excellent 

Certificate of Excellence

46

Vacation home in Shaftesbury

Dorset / Shaftesbury

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 30 mi
  • Child friendly
  • Car not necessary
Beautiful contemporary house set in an idyllic location in over an acre of land, situated near to the historical town of Shaftesbury. Ideal for entertaining large groups of up to 10 people for special occasions. The house has been built for luxury living, …see more

Certificate of Excellence

from $490 / night

$2,940 - $4,200 / week

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Responds fast!
avg. 2 hours 3 minutes

from $490 / night

(17) Excellent 

24

Vacation lodge in Shaftesbury

Dorset / Shaftesbury

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden
Saxon Lodge is a spacious, superbly-appointed Four Bedroom Holiday Lodge, identical to Abbey Lodge. Saxon Lodge offers the following: One King Bedroom; One Double Bedroom; Two Twin Bedrooms; Two full-size Bathrooms; Open-plan Lounge, Dining area and well-appointed Kitc …see more

from $126 / night

$882 / week

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from $126 / night

(8) Excellent 

23

Cottage rental in Shaftesbury

Dorset / Shaftesbury

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Ask about pets
  • Private garden
A rural retreat in the heart of Dorset, this terraced cottage comes with two bedrooms -- a double and twin. There is a comfortable living room with an open fire, a small library and a large eat-in kitchen with French windows leading to a garden with fine views. Picture …see more

from $105 / night

$700 - $1,267 / week

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from $105 / night

(19) Excellent 

Certificate of Excellence

20

Vacation studio in Higher Coombe

Shaftesbury / Higher Coombe

Studio 2 2 nights min

  • Studio
  • Sleeps 2
  • 2 nights min
  • Nearest beach 55 mi
  • Suitable for children age 5+
  • Ask about pets
Our 1-bedroom self-contained Studio Apartment is set in a beautiful quiet location on the edge of ancient woodland. It's perfect for individuals or couples or one parent and child. It's ideal as a weekend retreat for couples who want to escape the city for a short, roma …see more

Certificate of Excellence

from $98 / night

$637 / week

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Responds fast!
avg. 1 hour 28 minutes

from $98 / night

(14) Very Good 

16

Semley Vacation cottage rental

Shaftesbury / Semley

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 39 mi
  • Child friendly
  • Ask about pets
A 19th century family cottage surrounded by a very flowery garden and rolling countryside. The ground floor has the kitchen and a large dining room (with a piano that is reasonably in tune) and the master bedroom with en-suite bathroom. The first floor has a bright and …see more

from $140 / night

$763 - $1,385 / week

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Responds fast!
avg. 1 hour 6 minutes

from $140 / night

(20) Excellent 

Certificate of Excellence

31

Vacation cottage in Shaftesbury

Dorset / Shaftesbury

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Private garden
Summer Lodge is a beautiful refurbished cottage, it is cosy, comfortable, light and airy and furnished to a high standard, with thick new carpet throughout, comfortable quality beds and tasteful decor. New TV's lounge and both bedrooms, downstairs cloakroom, patio seati …see more

Certificate of Excellence

from $80 / night

$553 - $1,085 / week

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Responds fast!
avg. 1 hour 26 minutes

from $80 / night

12

Shaftesbury Vacation home rental

Dorset / Shaftesbury

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Child friendly
  • Pet friendly
  • Private garden
30 ACRES, HORSES, CHICKENS AND WOODLAND WALKS. SLEEPS 2+1 This cosy, but private detached lodge nestles in the grounds of the owners' smallholding. Your privacy is assured but the owners are always happy to offer help and advice on the local area and places of …see more

from $61 / night

$426 - $971 / week

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from $61 / night

9

Home rental in Cann

Shaftesbury / Cann

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Child friendly
  • Pet friendly
BARN CONVERSION SET WITHIN UNIQUE FARM IN 28 ACRES SLEEPS 4+1 This quaint semi-detached barn has been tastefully converted using redundant listed farm buildings and nestles within a 28 acres private specialist farm. Access to the barn is via a narrow lane. < …see more

from $69 / night

$483 - $1,133 / week

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from $69 / night

(29) Excellent 

Certificate of Excellence

29

Vacation cottage in Shaftesbury

Dorset / Shaftesbury

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Private garden
Easter cottage A beautiful mews cottage in the heart of the historic part of Shaftesbury with it's own courtyard parking, perfect for enjoying the town's atmosphere, an interesting and lovely location to holiday for all seasons, with so much to see and do, or jus …see more

Certificate of Excellence

from $80 / night

$553 - $1,043 / week

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Responds fast!
avg. 1 hour 26 minutes

from $80 / night

8

Vacation lodge in Shaftesbury

Dorset / Shaftesbury

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
Abbey Lodge a is spacious, well appointed four bedroom holiday Lodge, Identical to Saxon Lodge but is also pet friendly* . Abbey is also fitted to an exceptionally high standard. *although this Lodge is pet friendly we ensure it is to the same exceptionally high standa …see more

from $112 / night

$784 / week

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from $112 / night

(2) Very Good 

12

Shaftesbury Vacation lodge rental

Dorset / Shaftesbury

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 30 mi
  • Private garden
Little Lodge is our beautiful new designer lodge with its amazing Eco-Friendly Living Roof of shrubs that will adapt and change colours through the seasons. It is positioned inside our Lodge Park, overlooking the green space, which is a large exclusive area of just fiv …see more

from $97 / night

$677 / week

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from $97 / night

(6) Excellent 

22

Vacation cottage in Stour Provost

Shaftesbury / Stour Provost

2 3 3 nights min

  • 2 bedrooms
  • Sleeps 3
  • 3 nights min
  • Child friendly
Named after the family that lived here for four generations, Abbotts Cottage is a beautifully appointed cottage, perfect for two people and quietly situated along a winding country lane in the parish of Stour Provost, 3½ miles from Gillingham (main line railway station …see more

from $152 / night

$667 - $1,091 / week

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from $152 / night

(4) Excellent 

17

Vacation home in Shaftesbury

Dorset / Shaftesbury

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 25 mi
  • Child friendly
  • Private garden
Barbers Cottage is a listed, boutique-style holiday home located in the heart of the beautiful old Saxon town of Shaftesbury, Dorset bordering Wiltshire. Our popular cottage provides a comfortable base to explore the local area. Shaftesbury is renowned for its stunnin …see more

from $140 / night

$770 - $1,456 / week

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from $140 / night

(1) Very Good 

23

Vacation lodge in Shaftesbury

Dorset / Shaftesbury

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
Hardys Lodge named after Thomas Hardy, is a stunning, spacious two bedroom holiday Lodge, fitted to an exceptionally high standard. Hardy’s Lodge – named after famous Wessex Novelist Thomas Hardy – is a stunning and spacious Two Bedroom Holiday Lodge, fitted to a high …see more

from $100 / night

$696 / week

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from $100 / night

(11) Very Good 

22

Cottage rental in Shaftesbury

Dorset / Shaftesbury

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Pet friendly
Anvil Cottage is a converted Blacksmith's forge. It has large rooms and is very comfortable. Situated in a quiet hamlet, there are many footpaths close by. The property is on a smallholding with a few sheep,cattle,geese and chickens. The accommodation is arranged on one …see more

from $105 / night

$672 - $840 / week

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from $105 / night

21

Vacation home in Shaftesbury

Dorset / Shaftesbury

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Suitable for children age 5+
  • Private garden
It's like being in a village cottage, but you are walking distance to the town and shops, but perhaps the highlight of this house is the stylishly designed conservatory at the back. Flooded with light, it leads from both dining room and kitchen, and opens onto the patio …see more

from $252 / night

$1,763 / week

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from $252 / night

(3) Excellent 

23

Vacation home in Donhead St Andrew

Shaftesbury / Donhead St Andrew

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Nearest beach 50 mi
  • Private garden
Discreet, well appointed and very comfortable self-catering accomodation with dramatic uninterrupted views of Cranborne Chase. Sleeps 4 in 2 Super King bedrooms, one with a freestanding bath, the other with Twin beds as an option. Whether you are on a special nig …see more

from $392 / night

$2,744 / week

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from $392 / night

9

Vacation home in Donhead Saint Andrew

Shaftesbury / Donhead Saint Andrew

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
Please note this a private owner occupied house where we provide B&B. Guests normally check in Between 17.00 hrs and 18.00 hrs and guests, except by arrangement, are out during the day? The cost is £45.00 per person per night which includes full English cooked breakfas …see more

from $126 / night

$882 / week

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Responds fast!
avg. 3 hours 25 minutes

from $126 / night

13

Vacation lodge in Shaftesbury

Dorset / Shaftesbury

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
Melbury Lodge is a stunning, Luxury 3 bedroom Lodge. It is located within our Lodge Park in the foothills of the Saxon Hilltop Town of Shaftesbury and is set within beautiful countryside overlooking the green space and adjacent to Meadow and Lakeside walks with a variet …see more

from $112 / night

$784 / week

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from $112 / night

(1) Excellent 

16

Vacation home in Cann

Shaftesbury / Cann

3 4 7 nights min

  • 3 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Pet friendly
Situated in the heart of Dorset’s beautiful landscape of rolling hills and open farmland affording wonderful walking, there are a network of footpaths directly from the property. The area offers a wealth of pretty villages, sandy beaches and a coastline which has wor …see more

from $87 / night

$607 - $1,302 / week

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from $87 / night

(23) Excellent 

13

Cottage rental in Shaftesbury

Dorset / Shaftesbury

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 48 mi
  • Child friendly
  • Ask about pets
Gable Cottage is a 3 bedroom, character cottage built and designed originally as a life-sized dolls house with its own under ground air raid shelter. Gable Cottage sits in the heart of an Area of Outstanding Natural Beauty in the idyllic Dorset village of Berwick St …see more

Pricing unknown

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Pricing unknown

(1) Excellent 

11

Cann Vacation home rental

Shaftesbury / Cann

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Child friendly
  • Pet friendly
Situated in the heart of Dorset’s beautiful landscape of rolling hills and open farmland affording wonderful walking, there are a network of footpaths directly from the property. The area offers a wealth of pretty villages, sandy beaches and a coastline which has wor …see more

from $63 / night

$440 - $1,007 / week

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from $63 / night

(1) Good 

24

Cann Vacation home rental

Shaftesbury / Cann

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Private garden
Situated in the heart of Dorset’s beautiful landscape of rolling hills and open farmland affording wonderful walking, there are a network of footpaths directly from the property. The area offers a wealth of pretty villages, sandy beaches and a coastline which has wor …see more

from $170 / night

$1,190 - $2,799 / week

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from $170 / night

9

Vacation chalet in Shaftesbury

Dorset / Shaftesbury

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
Wessex Chalet is situated on a working dairy farm in North Dorset. An ideal getaway from busy working lives. With three ensuite bathrooms, one situated on the ground floor and suitable for the less abled guests. Open plan lounge with reclining sofa's, dining/kitchen wi …see more

from $189 / night

$632 - $1,522 / week

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Responds fast!
avg. 3 hours 42 minutes

from $189 / night

16

Shaftesbury Vacation home rental

Dorset / Shaftesbury

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
Magna Cottage is a 300-year-old self catering holiday rental nestling in a secluded valley at the end of a no-through-road on the Cranborne Chase, a mile from Ashmore in Dorset. This holiday cottage, a detached thatched flint property, is in an ideal location for an out …see more

from $292 / night

$1,389 - $3,090 / week

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from $292 / night

10

Vacation home in Shaftesbury

Dorset / Shaftesbury

3 5 3 nights min

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min
  • Child friendly
This Grade II listed stone cottage is located in the town of Shaftesbury and can sleep five people in two bedrooms. Sloe Cottage is a Grade II listed stone cottage in the town of Shaftesbury just twenty seven miles from Poole. The cottage sleeps five people and has two …see more

from $65 / night

$446 - $1,067 / week

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from $65 / night

(15) Excellent 

27

Vacation home in Shaftesbury

Dorset / Shaftesbury

4 6 3 nights min

  • 4 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 40 mi
  • Child friendly
  • Private garden
Updown Cottage is a C16th self catering holiday cottage, assessed as 5* with Gold Award from Visit Britain for all 11 years. The cottage is for currently for sale as we are moving closer to family but we are continuing to take bookings and look forward to hearing from e …see more

from $273 / night

$1,253 - $1,673 / week

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from $273 / night

14

Shaftesbury Vacation home rental

Dorset / Shaftesbury

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
This ground floor and basement apartment is in the town of Shaftesbury near to Salisbury and can sleep four people in two bedrooms. 1 Cann Court is a lovely ground floor and basement apartment situated in the town of Shaftesbury in south west England. The apartment ca …see more

from $69 / night

$475 - $1,011 / week

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from $69 / night

(12) Very Good 

15

Shaftesbury Vacation home accommodation

Dorset / Shaftesbury

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Pet friendly
Sleeping up to six people in two bedrooms, this self contained wing near Shaftesbury is in an ideal location for exploring Dorset. Majestic is a wing of the owners' cottage, 2 miles from Shaftesbury. The cottage has a double room and a room with a triple bunk, along wi …see more

from $66 / night

$455 - $1,123 / week

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from $66 / night

(3) Very Good 

17

Shaftesbury Vacation home rental

Dorset / Shaftesbury

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
The historic market-town of Shaftesbury sits 750 feet above sea-level, looking down onto the Blackmore Vale. Ryecross Farm Cottage is just half a mile from Shaftesbury, surrounded by idyllic farmland. Built in stone, the cottage has recently been converted to offer acc …see more

from $59 / night

$412 - $982 / week

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from $59 / night

54

Vacation home in Shaftesbury

Dorset / Shaftesbury

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Ask about children
  • Pet friendly
The peaceful location for this romantic Shepherd’s Hut in Dorset exudes a sense of calm and tranquility, and creates a wonderful setting for a romantic getaway. Angels Hut blends beautifully into its secluded woodland background on a private 65-acre farm, well away from …see more

from $168 / night

$1,176 / week

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from $168 / night

24

Home rental in Shaftesbury

Dorset / Shaftesbury

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Ask about children
  • Pet friendly
Majestically perched at the top of it's own private field, with magnificent views over rolling Dorset hills and the glorious valley below, sits Badgers Hut, a beautifully renovated Second World War gun carriage for two. This sublime countryside sanctuary is the perfect …see more

from $139 / night

$971 / week

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from $139 / night