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Shaftsbury Vacation Rentals

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50 rentals in Shaftsbury.
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200 Yr old Farmhouse on 45 acres, vacation rental in Shaftsbury
200 Yr old Farmhouse on 45 acres, vacation rental in Shaftsbury
200 Yr old Farmhouse on 45 acres, vacation rental in Shaftsbury

200 Yr old Farmhouse on 45 acres

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Escape the Chaos! Private cabin/ 40 Acres, vacation rental in Shaftsbury
Escape the Chaos! Private cabin/ 40 Acres, vacation rental in Shaftsbury
Escape the Chaos! Private cabin/ 40 Acres, vacation rental in Shaftsbury

Escape the Chaos! Private cabin/ 40 Acres

Rental Home
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Vermont Hillside Retreat, vacation rental in Shaftsbury
Vermont Hillside Retreat, vacation rental in Shaftsbury
Vermont Hillside Retreat, vacation rental in Shaftsbury

Vermont Hillside Retreat

Rental Home
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Stunning Post and Beam Art Studio/House, vacation rental in Shaftsbury
Stunning Post and Beam Art Studio/House, vacation rental in Shaftsbury
Stunning Post and Beam Art Studio/House, vacation rental in Shaftsbury

Stunning Post and Beam Art Studio/House

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Country Farmhouse with Views, vacation rental in Shaftsbury
Country Farmhouse with Views, vacation rental in Shaftsbury
Country Farmhouse with Views, vacation rental in Shaftsbury

Country Farmhouse with Views

Rental Home
4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Experience one of a kind Rustic Historic Vermont Barn interior newly renovated, vacation rental in Shaftsbury
Experience one of a kind Rustic Historic Vermont Barn interior newly renovated, vacation rental in Shaftsbury
Experience one of a kind Rustic Historic Vermont Barn interior newly renovated, vacation rental in Shaftsbury

Experience one of a kind Rustic Historic Vermont Barn interior newly renovated

Rental Home
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Romantic Bennington Vermont Cottage, vacation rental in Shaftsbury
Romantic Bennington Vermont Cottage, vacation rental in Shaftsbury
Romantic Bennington Vermont Cottage, vacation rental in Shaftsbury

Romantic Bennington Vermont Cottage

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Victorian Home in Bennington, Vermont, vacation rental in Shaftsbury
Victorian Home in Bennington, Vermont, vacation rental in Shaftsbury
Victorian Home in Bennington, Vermont, vacation rental in Shaftsbury

Victorian Home in Bennington, Vermont

Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Secluded Luxury In The Country, Close To Culture, vacation rental in Shaftsbury
Secluded Luxury In The Country, Close To Culture, vacation rental in Shaftsbury
Secluded Luxury In The Country, Close To Culture, vacation rental in Shaftsbury

Secluded Luxury In The Country, Close To Culture

Rental Home
4 bedrooms
3 bathrooms
Sleeps 24
Match: Sleeps
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Great Place to get away and have clean fresh air surround you!

Rental Home
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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1828 Vermont Cottage Feet From The Famous Battenkill River, vacation rental in Shaftsbury
1828 Vermont Cottage Feet From The Famous Battenkill River, vacation rental in Shaftsbury
1828 Vermont Cottage Feet From The Famous Battenkill River, vacation rental in Shaftsbury

1828 Vermont Cottage Feet From The Famous Battenkill River

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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All season lake front getaway!, vacation rental in Shaftsbury
All season lake front getaway!, vacation rental in Shaftsbury
All season lake front getaway!, vacation rental in Shaftsbury

All season lake front getaway!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Perfect for a peaceful get away in clean fresh Vermont air!

Rental Home
3 bedrooms
5 bathrooms
Sleeps 6
Match: Sleeps
More info
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Book your Summer Getaway Today!, vacation rental in Shaftsbury
Book your Summer Getaway Today!, vacation rental in Shaftsbury
Book your Summer Getaway Today!, vacation rental in Shaftsbury

Book your Summer Getaway Today!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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Quarry Hill Farm - stunning views - cozy yet expansive, vacation rental in Shaftsbury
Quarry Hill Farm - stunning views - cozy yet expansive, vacation rental in Shaftsbury
Quarry Hill Farm - stunning views - cozy yet expansive, vacation rental in Shaftsbury

Quarry Hill Farm - stunning views - cozy yet expansive

Rental Home
8 bedrooms
5 bathrooms
Sleeps 15
Match: Sleeps
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Historic 1913 Railroad Station Full of History, Views and Modern Amentities!, vacation rental in Shaftsbury
Historic 1913 Railroad Station Full of History, Views and Modern Amentities!, vacation rental in Shaftsbury
Historic 1913 Railroad Station Full of History, Views and Modern Amentities!, vacation rental in Shaftsbury

Historic 1913 Railroad Station Full of History, Views and Modern Amentities!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Historic Home in Old Bennington, Vermont, vacation rental in Shaftsbury
Historic Home in Old Bennington, Vermont, vacation rental in Shaftsbury
Historic Home in Old Bennington, Vermont, vacation rental in Shaftsbury

Historic Home in Old Bennington, Vermont

Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Perfect Country Cottage, vacation rental in Shaftsbury
Perfect Country Cottage, vacation rental in Shaftsbury
Perfect Country Cottage, vacation rental in Shaftsbury

Perfect Country Cottage

Rental Home
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful Southern Vermont Farmhouse on 100 Acres, Spectacular Views, Swim Pond, vacation rental in Shaftsbury
Beautiful Southern Vermont Farmhouse on 100 Acres, Spectacular Views, Swim Pond, vacation rental in Shaftsbury
Beautiful Southern Vermont Farmhouse on 100 Acres, Spectacular Views, Swim Pond, vacation rental in Shaftsbury

Beautiful Southern Vermont Farmhouse on 100 Acres, Spectacular Views, Swim Pond

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Peaceful Cottage Retreat, vacation rental in Shaftsbury
Peaceful Cottage Retreat, vacation rental in Shaftsbury
Peaceful Cottage Retreat, vacation rental in Shaftsbury

Peaceful Cottage Retreat

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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1K sf APT, Harvest to Holiday to Farm Activities, vacation rental in Shaftsbury
1K sf APT, Harvest to Holiday to Farm Activities, vacation rental in Shaftsbury
1K sf APT, Harvest to Holiday to Farm Activities, vacation rental in Shaftsbury

1K sf APT, Harvest to Holiday to Farm Activities

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Kayaker & Fly-fisher DREAM, private BattenKill waterfront super charming home, vacation rental in Shaftsbury
Kayaker & Fly-fisher DREAM, private BattenKill waterfront super charming home, vacation rental in Shaftsbury
Kayaker & Fly-fisher DREAM, private BattenKill waterfront super charming home, vacation rental in Shaftsbury

Kayaker & Fly-fisher DREAM, private BattenKill waterfront super charming home

Rental Home
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Bennington Guest Farmhouse, vacation rental in Shaftsbury
Bennington Guest Farmhouse, vacation rental in Shaftsbury
Bennington Guest Farmhouse, vacation rental in Shaftsbury

Bennington Guest Farmhouse

Rental Home
5 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
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New home in the heart of the Green Mountain Forest, vacation rental in Shaftsbury
New home in the heart of the Green Mountain Forest, vacation rental in Shaftsbury
New home in the heart of the Green Mountain Forest, vacation rental in Shaftsbury

New home in the heart of the Green Mountain Forest

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Historic 1780 Vermont Farm House with mountain views and 7 bedrooms, vacation rental in Shaftsbury
Historic 1780 Vermont Farm House with mountain views and 7 bedrooms, vacation rental in Shaftsbury
Historic 1780 Vermont Farm House with mountain views and 7 bedrooms, vacation rental in Shaftsbury

Historic 1780 Vermont Farm House with mountain views and 7 bedrooms

Rental Home
7 bedrooms
4 bathrooms
Sleeps 17
Match: Sleeps
More info
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Luxe 'Green Barn' Near Skiing w/ Mt Equinox Views!, vacation rental in Shaftsbury
Luxe 'Green Barn' Near Skiing w/ Mt Equinox Views!, vacation rental in Shaftsbury
Luxe 'Green Barn' Near Skiing w/ Mt Equinox Views!, vacation rental in Shaftsbury

Luxe 'Green Barn' Near Skiing w/ Mt Equinox Views!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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1920's Bennington Vermont Guest Barn, vacation rental in Shaftsbury
1920's Bennington Vermont Guest Barn, vacation rental in Shaftsbury
1920's Bennington Vermont Guest Barn, vacation rental in Shaftsbury

1920's Bennington Vermont Guest Barn

Rental Home
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
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Beautiful home near Manchester and the Mountains -, vacation rental in Shaftsbury
Beautiful home near Manchester and the Mountains -, vacation rental in Shaftsbury
Beautiful home near Manchester and the Mountains -, vacation rental in Shaftsbury

Beautiful home near Manchester and the Mountains -

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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The Henry House & Authentic Red Covered Bridge!, vacation rental in Shaftsbury
The Henry House & Authentic Red Covered Bridge!, vacation rental in Shaftsbury
The Henry House & Authentic Red Covered Bridge!, vacation rental in Shaftsbury

The Henry House & Authentic Red Covered Bridge!

Rental Home
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Levity Mountain: Farmhouse, Cottage, and Event Barn, vacation rental in Shaftsbury
Levity Mountain: Farmhouse, Cottage, and Event Barn, vacation rental in Shaftsbury
Levity Mountain: Farmhouse, Cottage, and Event Barn, vacation rental in Shaftsbury

Levity Mountain: Farmhouse, Cottage, and Event Barn

Rental Home
8 bedrooms
5 bathrooms
Sleeps 24
Match: Sleeps
More info
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NEW LISTING - Cozy Mountain Retreat on the Roaring Branch - dogs welcome, vacation rental in Shaftsbury
NEW LISTING - Cozy Mountain Retreat on the Roaring Branch - dogs welcome, vacation rental in Shaftsbury
NEW LISTING - Cozy Mountain Retreat on the Roaring Branch - dogs welcome, vacation rental in Shaftsbury

NEW LISTING - Cozy Mountain Retreat on the Roaring Branch - dogs welcome

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Spacious apartment in beautiful, historic Arlington VT, vacation rental in Shaftsbury
Spacious apartment in beautiful, historic Arlington VT, vacation rental in Shaftsbury
Spacious apartment in beautiful, historic Arlington VT, vacation rental in Shaftsbury

Spacious apartment in beautiful, historic Arlington VT

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Two Brooks Lodge - Beautiful Waterfront Vermont Retreat, vacation rental in Shaftsbury
Two Brooks Lodge - Beautiful Waterfront Vermont Retreat, vacation rental in Shaftsbury
Two Brooks Lodge - Beautiful Waterfront Vermont Retreat, vacation rental in Shaftsbury

Two Brooks Lodge - Beautiful Waterfront Vermont Retreat

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Historic c.1880 Victorian MA/VT border near Williams College MassMoCA Freshgrass, vacation rental in Shaftsbury
Historic c.1880 Victorian MA/VT border near Williams College MassMoCA Freshgrass, vacation rental in Shaftsbury
Historic c.1880 Victorian MA/VT border near Williams College MassMoCA Freshgrass, vacation rental in Shaftsbury

Historic c.1880 Victorian MA/VT border near Williams College MassMoCA Freshgrass

Rental Home
5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
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Awesome Mountain Views at this Studio with Loft, vacation rental in Shaftsbury
Awesome Mountain Views at this Studio with Loft, vacation rental in Shaftsbury
Awesome Mountain Views at this Studio with Loft, vacation rental in Shaftsbury

Awesome Mountain Views at this Studio with Loft

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Cozy 1 Bedroom farm stay cottage, vacation rental in Shaftsbury
Cozy 1 Bedroom farm stay cottage, vacation rental in Shaftsbury
Cozy 1 Bedroom farm stay cottage, vacation rental in Shaftsbury

Cozy 1 Bedroom farm stay cottage

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Stunning Views of the Equinox, vacation rental in Shaftsbury
Stunning Views of the Equinox, vacation rental in Shaftsbury
Stunning Views of the Equinox, vacation rental in Shaftsbury

Stunning Views of the Equinox

Rental Home
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
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Karin's Place, vacation rental in Shaftsbury
Karin's Place, vacation rental in Shaftsbury
Karin's Place, vacation rental in Shaftsbury

Karin's Place

Rental Home
7 bedrooms
6 bathrooms
Sleeps 20
Match: Sleeps
More info
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Lovely vintage home in Arlington Village close to Manchester Area and Bennington, vacation rental in Shaftsbury
Lovely vintage home in Arlington Village close to Manchester Area and Bennington, vacation rental in Shaftsbury
Lovely vintage home in Arlington Village close to Manchester Area and Bennington, vacation rental in Shaftsbury

Lovely vintage home in Arlington Village close to Manchester Area and Bennington

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Tentrr Signature Site - Fortunate Ewe Farm, vacation rental in Shaftsbury
Tentrr Signature Site - Fortunate Ewe Farm, vacation rental in Shaftsbury
Tentrr Signature Site - Fortunate Ewe Farm, vacation rental in Shaftsbury

Tentrr Signature Site - Fortunate Ewe Farm

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Charming, Fully Restored, Greek Revival House, Farmland Setting, vacation rental in Shaftsbury
Charming, Fully Restored, Greek Revival House, Farmland Setting, vacation rental in Shaftsbury
Charming, Fully Restored, Greek Revival House, Farmland Setting, vacation rental in Shaftsbury

Charming, Fully Restored, Greek Revival House, Farmland Setting

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Meme's High Mountain Lake House, vacation rental in Shaftsbury
Meme's High Mountain Lake House, vacation rental in Shaftsbury
Meme's High Mountain Lake House, vacation rental in Shaftsbury

Meme's High Mountain Lake House

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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Luxury Living High Above the Center of Town., vacation rental in Shaftsbury
Luxury Living High Above the Center of Town., vacation rental in Shaftsbury
Luxury Living High Above the Center of Town., vacation rental in Shaftsbury

Luxury Living High Above the Center of Town.

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Brand New Custom Log Cabin In The Green Mtn Forest, vacation rental in Shaftsbury
Brand New Custom Log Cabin In The Green Mtn Forest, vacation rental in Shaftsbury
Brand New Custom Log Cabin In The Green Mtn Forest, vacation rental in Shaftsbury

Brand New Custom Log Cabin In The Green Mtn Forest

Rental Home
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
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A Real Farm Vacation, vacation rental in Shaftsbury
A Real Farm Vacation, vacation rental in Shaftsbury
A Real Farm Vacation, vacation rental in Shaftsbury

A Real Farm Vacation

Rental Home
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
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Two Brooks Lodge, vacation rental in Shaftsbury
Two Brooks Lodge, vacation rental in Shaftsbury
Two Brooks Lodge, vacation rental in Shaftsbury

Two Brooks Lodge

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Unique Vermont Log Cabin Nestled in Red Mountains, vacation rental in Shaftsbury
Unique Vermont Log Cabin Nestled in Red Mountains, vacation rental in Shaftsbury
Unique Vermont Log Cabin Nestled in Red Mountains, vacation rental in Shaftsbury

Unique Vermont Log Cabin Nestled in Red Mountains

Rental Home
3 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Best Western Bennington - Deluxe King Bed #5, vacation rental in Shaftsbury
Best Western Bennington - Deluxe King Bed #5, vacation rental in Shaftsbury
Best Western Bennington - Deluxe King Bed #5, vacation rental in Shaftsbury

Best Western Bennington - Deluxe King Bed #5

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Best Western Bennington - Deluxe King Bed #4, vacation rental in Shaftsbury
Best Western Bennington - Deluxe King Bed #4, vacation rental in Shaftsbury
Best Western Bennington - Deluxe King Bed #4, vacation rental in Shaftsbury

Best Western Bennington - Deluxe King Bed #4

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Retreat to a beautiful 12 bedroom Inn complete with Chef's Kitchen, vacation rental in Shaftsbury
Retreat to a beautiful 12 bedroom Inn complete with Chef's Kitchen, vacation rental in Shaftsbury
Retreat to a beautiful 12 bedroom Inn complete with Chef's Kitchen, vacation rental in Shaftsbury

Retreat to a beautiful 12 bedroom Inn complete with Chef's Kitchen

Rental Home
12 bedrooms
13 bathrooms
Sleeps 20
Match: Sleeps
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