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Shaftsbury Holiday Apartments

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

200 Yr old Farmhouse on 45 acres

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
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Mountains, farm animals, pond, old barn, hiking trails- quintessential Vermont!, holiday rental in Shaftsbury
Mountains, farm animals, pond, old barn, hiking trails- quintessential Vermont!, holiday rental in Shaftsbury
Mountains, farm animals, pond, old barn, hiking trails- quintessential Vermont!, holiday rental in Shaftsbury

Mountains, farm animals, pond, old barn, hiking trails- quintessential Vermont!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 7
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Vermont Hillside Retreat, holiday rental in Shaftsbury
Vermont Hillside Retreat, holiday rental in Shaftsbury
Vermont Hillside Retreat, holiday rental in Shaftsbury

Vermont Hillside Retreat

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 12
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Stunning Post and Beam Art Studio/House, holiday rental in Shaftsbury
Stunning Post and Beam Art Studio/House, holiday rental in Shaftsbury
Stunning Post and Beam Art Studio/House, holiday rental in Shaftsbury

Stunning Post and Beam Art Studio/House

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
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Country Farmhouse with Views, holiday rental in Shaftsbury
Country Farmhouse with Views, holiday rental in Shaftsbury
Country Farmhouse with Views, holiday rental in Shaftsbury

Country Farmhouse with Views

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 6
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Gracious Vermont Home Epic Mountain Views — EV Charger, holiday rental in Shaftsbury
Gracious Vermont Home Epic Mountain Views — EV Charger, holiday rental in Shaftsbury
Gracious Vermont Home Epic Mountain Views — EV Charger, holiday rental in Shaftsbury

Gracious Vermont Home Epic Mountain Views — EV Charger

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
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Private home on 37 acres with stunning mountain views, holiday rental in Shaftsbury
Private home on 37 acres with stunning mountain views, holiday rental in Shaftsbury
Private home on 37 acres with stunning mountain views, holiday rental in Shaftsbury

Private home on 37 acres with stunning mountain views

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
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Romantic Bennington Vermont Cottage, holiday rental in Shaftsbury
Romantic Bennington Vermont Cottage, holiday rental in Shaftsbury
Romantic Bennington Vermont Cottage, holiday rental in Shaftsbury

Romantic Bennington Vermont Cottage

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
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Victorian Home in Bennington, Vermont, holiday rental in Shaftsbury
Victorian Home in Bennington, Vermont, holiday rental in Shaftsbury
Victorian Home in Bennington, Vermont, holiday rental in Shaftsbury

Victorian Home in Bennington, Vermont

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Great Place to get away and have clean fresh air surround you!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 6
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Secluded Luxury In The Country, Close To Culture, holiday rental in Shaftsbury
Secluded Luxury In The Country, Close To Culture, holiday rental in Shaftsbury
Secluded Luxury In The Country, Close To Culture, holiday rental in Shaftsbury

Secluded Luxury In The Country, Close To Culture

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 24
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1828 Vermont Cottage Feet From The Famous Battenkill River, holiday rental in Shaftsbury
1828 Vermont Cottage Feet From The Famous Battenkill River, holiday rental in Shaftsbury
1828 Vermont Cottage Feet From The Famous Battenkill River, holiday rental in Shaftsbury

1828 Vermont Cottage Feet From The Famous Battenkill River

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
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Perfect for a peaceful get away in clean fresh Vermont air!

Holiday Rental House
3 bedrooms
5 bathrooms
Sleeps 6
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Come hike the mountains and trails of Vermont and NY this summer !, holiday rental in Shaftsbury
Come hike the mountains and trails of Vermont and NY this summer !, holiday rental in Shaftsbury
Come hike the mountains and trails of Vermont and NY this summer !, holiday rental in Shaftsbury

Come hike the mountains and trails of Vermont and NY this summer !

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
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Quarry Hill Farm - stunning views - cozy yet expansive, holiday rental in Shaftsbury
Quarry Hill Farm - stunning views - cozy yet expansive, holiday rental in Shaftsbury
Quarry Hill Farm - stunning views - cozy yet expansive, holiday rental in Shaftsbury

Quarry Hill Farm - stunning views - cozy yet expansive

Holiday Rental House
8 bedrooms
5 bathrooms
Sleeps 15
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Historic railway station from 1913 full of history, views and modern amentities!, holiday rental in Shaftsbury
Historic railway station from 1913 full of history, views and modern amentities!, holiday rental in Shaftsbury
Historic railway station from 1913 full of history, views and modern amentities!, holiday rental in Shaftsbury

Historic railway station from 1913 full of history, views and modern amentities!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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Historic Home in Old Bennington, Vermont, holiday rental in Shaftsbury
Historic Home in Old Bennington, Vermont, holiday rental in Shaftsbury
Historic Home in Old Bennington, Vermont, holiday rental in Shaftsbury

Historic Home in Old Bennington, Vermont

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Kayaker & Fly-fisher DREAM, private BattenKill waterfront super charming home, holiday rental in Shaftsbury
Kayaker & Fly-fisher DREAM, private BattenKill waterfront super charming home, holiday rental in Shaftsbury
Kayaker & Fly-fisher DREAM, private BattenKill waterfront super charming home, holiday rental in Shaftsbury

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
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FARM-TO-TABLE eating, a good hot tub soak, S'mores around the FIRE PIT!, holiday rental in Shaftsbury
FARM-TO-TABLE eating, a good hot tub soak, S'mores around the FIRE PIT!, holiday rental in Shaftsbury
FARM-TO-TABLE eating, a good hot tub soak, S'mores around the FIRE PIT!, holiday rental in Shaftsbury

FARM-TO-TABLE eating, a good hot tub soak, S'mores around the FIRE PIT!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Bennington Guest Farmhouse, holiday rental in Shaftsbury
Bennington Guest Farmhouse, holiday rental in Shaftsbury
Bennington Guest Farmhouse, holiday rental in Shaftsbury

Bennington Guest Farmhouse

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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New home in the heart of the Green Mountain Forest, holiday rental in Shaftsbury
New home in the heart of the Green Mountain Forest, holiday rental in Shaftsbury
New home in the heart of the Green Mountain Forest, holiday rental in Shaftsbury

New home in the heart of the Green Mountain Forest

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful home near Manchester and the Mountains -, holiday rental in Shaftsbury
Beautiful home near Manchester and the Mountains -, holiday rental in Shaftsbury
Beautiful home near Manchester and the Mountains -, holiday rental in Shaftsbury

Beautiful home near Manchester and the Mountains -

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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1920's Bennington Vermont Guest Barn, holiday rental in Shaftsbury
1920's Bennington Vermont Guest Barn, holiday rental in Shaftsbury
1920's Bennington Vermont Guest Barn, holiday rental in Shaftsbury

1920's Bennington Vermont Guest Barn

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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The Henry House & Authentic Red Covered Bridge!, holiday rental in Shaftsbury
The Henry House & Authentic Red Covered Bridge!, holiday rental in Shaftsbury
The Henry House & Authentic Red Covered Bridge!, holiday rental in Shaftsbury

The Henry House & Authentic Red Covered Bridge!

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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NEW LISTING - Cozy Mountain Retreat on the Roaring Branch - dogs welcome, holiday rental in Shaftsbury
NEW LISTING - Cozy Mountain Retreat on the Roaring Branch - dogs welcome, holiday rental in Shaftsbury
NEW LISTING - Cozy Mountain Retreat on the Roaring Branch - dogs welcome, holiday rental in Shaftsbury

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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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✰ Two Brooks Lodge - Beautiful Waterfront Vermont Retreat, holiday rental in Shaftsbury
✰ Two Brooks Lodge - Beautiful Waterfront Vermont Retreat, holiday rental in Shaftsbury
✰ Two Brooks Lodge - Beautiful Waterfront Vermont Retreat, holiday rental in Shaftsbury

✰ Two Brooks Lodge - Beautiful Waterfront Vermont Retreat

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Cozy 1 Bedroom farm stay cottage, holiday rental in Shaftsbury
Cozy 1 Bedroom farm stay cottage, holiday rental in Shaftsbury
Cozy 1 Bedroom farm stay cottage, holiday rental in Shaftsbury

Cozy 1 Bedroom farm stay cottage

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Karin's Place, holiday rental in Shaftsbury
Karin's Place, holiday rental in Shaftsbury
Karin's Place, holiday rental in Shaftsbury

Karin's Place

Holiday Rental House
7 bedrooms
6 bathrooms
Sleeps 20
Match: Sleeps
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Lovely vintage home in Arlington Village close to Manchester Area and Bennington, holiday rental in Shaftsbury
Lovely vintage home in Arlington Village close to Manchester Area and Bennington, holiday rental in Shaftsbury
Lovely vintage home in Arlington Village close to Manchester Area and Bennington, holiday rental in Shaftsbury

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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Meme's High Mountain Lake House, holiday rental in Shaftsbury
Meme's High Mountain Lake House, holiday rental in Shaftsbury
Meme's High Mountain Lake House, holiday rental in Shaftsbury

Meme's High Mountain Lake House

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Luxury Living High Above the Center of Town., holiday rental in Shaftsbury
Luxury Living High Above the Center of Town., holiday rental in Shaftsbury
Luxury Living High Above the Center of Town., holiday rental in Shaftsbury

Luxury Living High Above the Center of Town.

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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A Real Farm Vacation, holiday rental in Shaftsbury
A Real Farm Vacation, holiday rental in Shaftsbury
A Real Farm Vacation, holiday rental in Shaftsbury

A Real Farm Vacation

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Two Brooks Lodge, holiday rental in Shaftsbury
Two Brooks Lodge, holiday rental in Shaftsbury
Two Brooks Lodge, holiday rental in Shaftsbury

Two Brooks Lodge

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Unique Vermont Log Cabin Nestled in Red Mountains, holiday rental in Shaftsbury
Unique Vermont Log Cabin Nestled in Red Mountains, holiday rental in Shaftsbury
Unique Vermont Log Cabin Nestled in Red Mountains, holiday rental in Shaftsbury

Unique Vermont Log Cabin Nestled in Red Mountains

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

Best Western Bennington - Deluxe King Bed #5

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Best Western Bennington - Deluxe King Bed #4, holiday rental in Shaftsbury
Best Western Bennington - Deluxe King Bed #4, holiday rental in Shaftsbury
Best Western Bennington - Deluxe King Bed #4, holiday rental in Shaftsbury

Best Western Bennington - Deluxe King Bed #4

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Comfortable & Charming Country Abode in lovely Vermont, holiday rental in Shaftsbury
Comfortable & Charming Country Abode in lovely Vermont, holiday rental in Shaftsbury
Comfortable & Charming Country Abode in lovely Vermont, holiday rental in Shaftsbury

Comfortable & Charming Country Abode in lovely Vermont

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Nature Lovers Paradise Converted Barn, holiday rental in Shaftsbury
Nature Lovers Paradise Converted Barn, holiday rental in Shaftsbury
Nature Lovers Paradise Converted Barn, holiday rental in Shaftsbury

Nature Lovers Paradise Converted Barn

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
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Grand 1800's farmhouse 8+ BRs 6 mi to Bennington VT. Great for groups, reunions., holiday rental in Shaftsbury
Grand 1800's farmhouse 8+ BRs 6 mi to Bennington VT. Great for groups, reunions., holiday rental in Shaftsbury
Grand 1800's farmhouse 8+ BRs 6 mi to Bennington VT. Great for groups, reunions., holiday rental in Shaftsbury

Grand 1800's farmhouse 8+ BRs 6 mi to Bennington VT. Great for groups, reunions.

Holiday Rental House
8 bedrooms
3 bathrooms
Sleeps 23
Match: Sleeps
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Victorian mansion's Jim-Dandy Suite w/ breakfast, holiday rental in Shaftsbury
Victorian mansion's Jim-Dandy Suite w/ breakfast, holiday rental in Shaftsbury
Victorian mansion's Jim-Dandy Suite w/ breakfast, holiday rental in Shaftsbury

Victorian mansion's Jim-Dandy Suite w/ breakfast

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Affordable & Convenient Arlington Apt (Near Horse Show), holiday rental in Shaftsbury
Affordable & Convenient Arlington Apt (Near Horse Show), holiday rental in Shaftsbury
Affordable & Convenient Arlington Apt (Near Horse Show), holiday rental in Shaftsbury

Affordable & Convenient Arlington Apt (Near Horse Show)

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Spacious 2nd floor apartment steps from popular corner market., holiday rental in Shaftsbury
Spacious 2nd floor apartment steps from popular corner market., holiday rental in Shaftsbury
Spacious 2nd floor apartment steps from popular corner market., holiday rental in Shaftsbury

Spacious 2nd floor apartment steps from popular corner market.

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Best Western Bennington - Deluxe King Bed #3, holiday rental in Shaftsbury
Best Western Bennington - Deluxe King Bed #3, holiday rental in Shaftsbury
Best Western Bennington - Deluxe King Bed #3, holiday rental in Shaftsbury

Best Western Bennington - Deluxe King Bed #3

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Bright 3-Bedroom Historical Cottage w/ pool table, holiday rental in Shaftsbury
Bright 3-Bedroom Historical Cottage w/ pool table, holiday rental in Shaftsbury
Bright 3-Bedroom Historical Cottage w/ pool table, holiday rental in Shaftsbury

Bright 3-Bedroom Historical Cottage w/ pool table

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Historic 18th Century Farmhouse + Hot Tub + Stunning Gardens + Koi Pond + Skiing, holiday rental in Shaftsbury
Historic 18th Century Farmhouse + Hot Tub + Stunning Gardens + Koi Pond + Skiing, holiday rental in Shaftsbury
Historic 18th Century Farmhouse + Hot Tub + Stunning Gardens + Koi Pond + Skiing, holiday rental in Shaftsbury

Historic 18th Century Farmhouse + Hot Tub + Stunning Gardens + Koi Pond + Skiing

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Best Western Bennington - Deluxe King Bed #1, holiday rental in Shaftsbury
Best Western Bennington - Deluxe King Bed #1, holiday rental in Shaftsbury
Best Western Bennington - Deluxe King Bed #1, holiday rental in Shaftsbury

Best Western Bennington - Deluxe King Bed #1

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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CUTE 1 BEDROOM APARTMENT WITHIN A FARM SETTING, holiday rental in Shaftsbury
CUTE 1 BEDROOM APARTMENT WITHIN A FARM SETTING, holiday rental in Shaftsbury
CUTE 1 BEDROOM APARTMENT WITHIN A FARM SETTING, holiday rental in Shaftsbury

CUTE 1 BEDROOM APARTMENT WITHIN A FARM SETTING

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Lake life at Woodford Cottage, holiday rental in Shaftsbury
Lake life at Woodford Cottage, holiday rental in Shaftsbury
Lake life at Woodford Cottage, holiday rental in Shaftsbury

Lake life at Woodford Cottage

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Best Western Bennington - Deluxe King Bed #2, holiday rental in Shaftsbury
Best Western Bennington - Deluxe King Bed #2, holiday rental in Shaftsbury
Best Western Bennington - Deluxe King Bed #2, holiday rental in Shaftsbury

Best Western Bennington - Deluxe King Bed #2

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Downtown Victorian House, holiday rental in Shaftsbury
Downtown Victorian House, holiday rental in Shaftsbury
Downtown Victorian House, holiday rental in Shaftsbury

Downtown Victorian House

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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