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North Bennington Vacation Rentals

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49 rentals in North Bennington.
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Romantic Bennington Vermont Cottage, vacation rental in North Bennington
Romantic Bennington Vermont Cottage, vacation rental in North Bennington
Romantic Bennington Vermont Cottage, vacation rental in North Bennington

Romantic Bennington Vermont Cottage

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Bennington Guest Farmhouse, vacation rental in North Bennington
Bennington Guest Farmhouse, vacation rental in North Bennington
Bennington Guest Farmhouse, vacation rental in North Bennington

Bennington Guest Farmhouse

Rental Home
5 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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1920's Bennington Vermont Guest Barn, vacation rental in North Bennington
1920's Bennington Vermont Guest Barn, vacation rental in North Bennington
1920's Bennington Vermont Guest Barn, vacation rental in North Bennington

1920's Bennington Vermont Guest Barn

Rental Home
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Bright 3-Bedroom Historical Cottage w/ pool table, vacation rental in North Bennington
Bright 3-Bedroom Historical Cottage w/ pool table, vacation rental in North Bennington
Bright 3-Bedroom Historical Cottage w/ pool table, vacation rental in North Bennington

Bright 3-Bedroom Historical Cottage w/ pool table

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cozy Converted Barn on Secluded 6.5 acres, vacation rental in North Bennington
Cozy Converted Barn on Secluded 6.5 acres, vacation rental in North Bennington
Cozy Converted Barn on Secluded 6.5 acres, vacation rental in North Bennington

Cozy Converted Barn on Secluded 6.5 acres

Rental Home
1 bedroom
1 bathroom
Sleeps 8
Match: Sleeps
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Victorian Home in Bennington, Vermont, vacation rental in North Bennington
Victorian Home in Bennington, Vermont, vacation rental in North Bennington
Victorian Home in Bennington, Vermont, vacation rental in North Bennington

Victorian Home in Bennington, Vermont

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

Secluded Luxury In The Country, Close To Culture

Rental Home
4 bedrooms
2 bathrooms
Sleeps 24
Match: Sleeps
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Great Place to get away and have clean fresh air surround you!, vacation rental in North Bennington
Great Place to get away and have clean fresh air surround you!, vacation rental in North Bennington
Great Place to get away and have clean fresh air surround you!, vacation rental in North Bennington

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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Perfect for a peaceful get away in clean fresh Vermont air!, vacation rental in North Bennington
Perfect for a peaceful get away in clean fresh Vermont air!, vacation rental in North Bennington
Perfect for a peaceful get away in clean fresh Vermont air!, vacation rental in North Bennington

Perfect for a peaceful get away in clean fresh Vermont air!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Book now for the  Holidays � and spend your evenings by the fire �., vacation rental in North Bennington
Book now for the  Holidays � and spend your evenings by the fire �., vacation rental in North Bennington
Book now for the  Holidays � and spend your evenings by the fire �., vacation rental in North Bennington

Book now for the Holidays � and spend your evenings by the fire �.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
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200 Yr old Farmhouse on 45 acres, vacation rental in North Bennington
200 Yr old Farmhouse on 45 acres, vacation rental in North Bennington
200 Yr old Farmhouse on 45 acres, vacation rental in North Bennington

200 Yr old Farmhouse on 45 acres

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Quarry Hill Farm - stunning views - cozy yet expansive, vacation rental in North Bennington
Quarry Hill Farm - stunning views - cozy yet expansive, vacation rental in North Bennington
Quarry Hill Farm - stunning views - cozy yet expansive, vacation rental in North Bennington

Quarry Hill Farm - stunning views - cozy yet expansive

Rental Home
8 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Historic Home in Old Bennington, Vermont, vacation rental in North Bennington
Historic Home in Old Bennington, Vermont, vacation rental in North Bennington
Historic Home in Old Bennington, Vermont, vacation rental in North Bennington

Historic Home in Old Bennington, Vermont

Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Mountains, farm animals, pond, old barn, hiking trails- quintessential Vermont!, vacation rental in North Bennington
Mountains, farm animals, pond, old barn, hiking trails- quintessential Vermont!, vacation rental in North Bennington
Mountains, farm animals, pond, old barn, hiking trails- quintessential Vermont!, vacation rental in North Bennington

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

Rental Home
2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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New home in the heart of the Green Mountain Forest, vacation rental in North Bennington
New home in the heart of the Green Mountain Forest, vacation rental in North Bennington
New home in the heart of the Green Mountain Forest, vacation rental in North Bennington

New home in the heart of the Green Mountain Forest

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cozy Woodford Lakefront Cottage, vacation rental in North Bennington
Cozy Woodford Lakefront Cottage, vacation rental in North Bennington
Cozy Woodford Lakefront Cottage, vacation rental in North Bennington

Cozy Woodford Lakefront Cottage

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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VINTAGE BARN APT, POOL, HOT TUB, FIRE PIT, GRILL, vacation rental in North Bennington
VINTAGE BARN APT, POOL, HOT TUB, FIRE PIT, GRILL, vacation rental in North Bennington
VINTAGE BARN APT, POOL, HOT TUB, FIRE PIT, GRILL, vacation rental in North Bennington

VINTAGE BARN APT, POOL, HOT TUB, FIRE PIT, GRILL

Rental Home
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Historic School House, vacation rental in North Bennington
Historic School House, vacation rental in North Bennington
Historic School House, vacation rental in North Bennington

Historic School House

Rental Home
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Stunning Post and Beam Art Studio/House, vacation rental in North Bennington
Stunning Post and Beam Art Studio/House, vacation rental in North Bennington
Stunning Post and Beam Art Studio/House, vacation rental in North Bennington

Stunning Post and Beam Art Studio/House

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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NEW LISTING - Cozy Mountain Retreat on the Roaring Branch - dogs welcome, vacation rental in North Bennington
NEW LISTING - Cozy Mountain Retreat on the Roaring Branch - dogs welcome, vacation rental in North Bennington
NEW LISTING - Cozy Mountain Retreat on the Roaring Branch - dogs welcome, vacation rental in North Bennington

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

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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✰ Two Brooks Lodge - Beautiful Waterfront Vermont Retreat, vacation rental in North Bennington
✰ Two Brooks Lodge - Beautiful Waterfront Vermont Retreat, vacation rental in North Bennington
✰ Two Brooks Lodge - Beautiful Waterfront Vermont Retreat, vacation rental in North Bennington

✰ Two Brooks Lodge - Beautiful Waterfront Vermont Retreat

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

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

Rental Home
5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Cozy 1 Bedroom farm stay cottage, vacation rental in North Bennington
Cozy 1 Bedroom farm stay cottage, vacation rental in North Bennington
Cozy 1 Bedroom farm stay cottage, vacation rental in North Bennington

Cozy 1 Bedroom farm stay cottage

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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NEW! Bennington Cabin w/ Deck & Views of 3 States!, vacation rental in North Bennington
NEW! Bennington Cabin w/ Deck & Views of 3 States!, vacation rental in North Bennington
NEW! Bennington Cabin w/ Deck & Views of 3 States!, vacation rental in North Bennington

NEW! Bennington Cabin w/ Deck & Views of 3 States!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Karin's Place, vacation rental in North Bennington
Karin's Place, vacation rental in North Bennington
Karin's Place, vacation rental in North Bennington

Karin's Place

Rental Home
7 bedrooms
6 bathrooms
Sleeps 20
Match: Sleeps
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Country Farmhouse with Views, vacation rental in North Bennington
Country Farmhouse with Views, vacation rental in North Bennington
Country Farmhouse with Views, vacation rental in North Bennington

Country Farmhouse with Views

Rental Home
4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Artists' Dream Space in the Center of Downtown Be, vacation rental in North Bennington
Artists' Dream Space in the Center of Downtown Be, vacation rental in North Bennington
Artists' Dream Space in the Center of Downtown Be, vacation rental in North Bennington

Artists' Dream Space in the Center of Downtown Be

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Tentrr Signature Site - Fortunate Ewe Farm, vacation rental in North Bennington
Tentrr Signature Site - Fortunate Ewe Farm, vacation rental in North Bennington
Tentrr Signature Site - Fortunate Ewe Farm, vacation rental in North Bennington

Tentrr Signature Site - Fortunate Ewe Farm

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Nuthatch, vacation rental in North Bennington
Tentrr Signature Site - Nuthatch, vacation rental in North Bennington
Tentrr Signature Site - Nuthatch, vacation rental in North Bennington

Tentrr Signature Site - Nuthatch

Rental Home
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Charming, Fully Restored, Greek Revival House, Farmland Setting, vacation rental in North Bennington
Charming, Fully Restored, Greek Revival House, Farmland Setting, vacation rental in North Bennington
Charming, Fully Restored, Greek Revival House, Farmland Setting, vacation rental in North Bennington

Charming, Fully Restored, Greek Revival House, Farmland Setting

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

Meme's High Mountain Lake House

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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“One of a kind”  “cozy” “chic” Renovated Barn with modern rustic charm, vacation rental in North Bennington
“One of a kind”  “cozy” “chic” Renovated Barn with modern rustic charm, vacation rental in North Bennington
“One of a kind”  “cozy” “chic” Renovated Barn with modern rustic charm, vacation rental in North Bennington

“One of a kind” “cozy” “chic” Renovated Barn with modern rustic charm

Rental Home
3 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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Two Brooks Lodge, vacation rental in North Bennington
Two Brooks Lodge, vacation rental in North Bennington
Two Brooks Lodge, vacation rental in North Bennington

Two Brooks Lodge

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Best Western Bennington - Deluxe King Bed #5, vacation rental in North Bennington
Best Western Bennington - Deluxe King Bed #5, vacation rental in North Bennington
Best Western Bennington - Deluxe King Bed #5, vacation rental in North Bennington

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 North Bennington
Best Western Bennington - Deluxe King Bed #4, vacation rental in North Bennington
Best Western Bennington - Deluxe King Bed #4, vacation rental in North Bennington

Best Western Bennington - Deluxe King Bed #4

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Nature Lovers Paradise Converted Barn, vacation rental in North Bennington
Nature Lovers Paradise Converted Barn, vacation rental in North Bennington
Nature Lovers Paradise Converted Barn, vacation rental in North Bennington

Nature Lovers Paradise Converted Barn

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Grand farmhouse, big groups, has it all 1 mi to VT, vacation rental in North Bennington
Grand farmhouse, big groups, has it all 1 mi to VT, vacation rental in North Bennington
Grand farmhouse, big groups, has it all 1 mi to VT, vacation rental in North Bennington

Grand farmhouse, big groups, has it all 1 mi to VT

Rental Home
8 bedrooms
3 bathrooms
Sleeps 23
Match: Sleeps
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Victorian mansion's Jim-Dandy Suite w/ breakfast, vacation rental in North Bennington
Victorian mansion's Jim-Dandy Suite w/ breakfast, vacation rental in North Bennington
Victorian mansion's Jim-Dandy Suite w/ breakfast, vacation rental in North Bennington

Victorian mansion's Jim-Dandy Suite w/ breakfast

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Stunning Mountain View Vermont Farm Stay - Hot Tub, vacation rental in North Bennington
Stunning Mountain View Vermont Farm Stay - Hot Tub, vacation rental in North Bennington
Stunning Mountain View Vermont Farm Stay - Hot Tub, vacation rental in North Bennington

Stunning Mountain View Vermont Farm Stay - Hot Tub

Rental Home
5 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
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Spacious 2nd floor apartment steps from popular corner market., vacation rental in North Bennington
Spacious 2nd floor apartment steps from popular corner market., vacation rental in North Bennington
Spacious 2nd floor apartment steps from popular corner market., vacation rental in North Bennington

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, vacation rental in North Bennington
Best Western Bennington - Deluxe King Bed #3, vacation rental in North Bennington
Best Western Bennington - Deluxe King Bed #3, vacation rental in North Bennington

Best Western Bennington - Deluxe King Bed #3

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Private home on 37 acres with stunning mountain views, vacation rental in North Bennington
Private home on 37 acres with stunning mountain views, vacation rental in North Bennington
Private home on 37 acres with stunning mountain views, vacation rental in North Bennington

Private home on 37 acres with stunning mountain views

Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Modern 18th Century Farmhouse|Hot Tub|Stratton+Bromley Skiing|Pets Welcome, vacation rental in North Bennington
Modern 18th Century Farmhouse|Hot Tub|Stratton+Bromley Skiing|Pets Welcome, vacation rental in North Bennington
Modern 18th Century Farmhouse|Hot Tub|Stratton+Bromley Skiing|Pets Welcome, vacation rental in North Bennington

Modern 18th Century Farmhouse|Hot Tub|Stratton+Bromley Skiing|Pets Welcome

Rental Home
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Best Western Bennington - Deluxe King Bed #1, vacation rental in North Bennington
Best Western Bennington - Deluxe King Bed #1, vacation rental in North Bennington
Best Western Bennington - Deluxe King Bed #1, vacation rental in North Bennington

Best Western Bennington - Deluxe King Bed #1

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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CUTE 1 BEDROOM APARTMENT WITHIN A FARM SETTING, vacation rental in North Bennington
CUTE 1 BEDROOM APARTMENT WITHIN A FARM SETTING, vacation rental in North Bennington
CUTE 1 BEDROOM APARTMENT WITHIN A FARM SETTING, vacation rental in North Bennington

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, vacation rental in North Bennington
Lake life at Woodford Cottage, vacation rental in North Bennington
Lake life at Woodford Cottage, vacation rental in North Bennington

Lake life at Woodford Cottage

Rental Home
2 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Exceptionally beautiful and spacious country home, vacation rental in North Bennington
Exceptionally beautiful and spacious country home, vacation rental in North Bennington
Exceptionally beautiful and spacious country home, vacation rental in North Bennington

Exceptionally beautiful and spacious country home

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Best Western Bennington - Deluxe King Bed #2, vacation rental in North Bennington
Best Western Bennington - Deluxe King Bed #2, vacation rental in North Bennington
Best Western Bennington - Deluxe King Bed #2, vacation rental in North Bennington

Best Western Bennington - Deluxe King Bed #2

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Studio style farm stay, vacation rental in North Bennington
Studio style farm stay, vacation rental in North Bennington
Studio style farm stay, vacation rental in North Bennington

Studio style farm stay

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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FARM-TO-TABLE eating, a good hot tub soak, S'mores around the FIRE PIT!, vacation rental in North Bennington
FARM-TO-TABLE eating, a good hot tub soak, S'mores around the FIRE PIT!, vacation rental in North Bennington
FARM-TO-TABLE eating, a good hot tub soak, S'mores around the FIRE PIT!, vacation rental in North Bennington

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

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 1
More info
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Frequently Asked Questions about North Bennington