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Search results; Over 1,000 homes in Bennington

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Top guest favourite
Home in Bennington
The Vermont Farmhouse|Hiking|Dog Trails|Village
2 bedrooms, 3 beds, 2.5 private bathrooms
20–25 Sept
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5.0 out of 5 average rating, 137 reviews
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Cottage in Shaftsbury
Rollin Cottage
2 bedrooms, 2 queen beds, 1 bathroom
27 Oct – 1 Nov
4.97 out of 5 average rating, 176 reviews
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Cabin in Bennington
Mount Anthony Cabin
2 bedrooms, 3 beds, 1 bathroom
25–30 Oct
4.96 out of 5 average rating, 101 reviews
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Room in Bennington
Quiet country retreat 311 Rice Lane Bennington, VT
1 queen bed, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 86 reviews
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Flat in Bennington
Cozy Loft steps from VT Downtown
1 bedroom, 1 queen bed, 1 bathroom
24–29 Sept
4.93 out of 5 average rating, 108 reviews
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Home in Bennington
Cozy Mountain Retreat - Museums, Trails & Colleges
2 bedrooms, 3 beds, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 8 reviews
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Room in Bennington
E and E’s B and B Queen Bed Rm+ Pool & Hot Tub
1 queen bed, 1 bathroom
16–22 Sept
4.99 out of 5 average rating, 140 reviews
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Boutique hotel in Bennington
Harwood Hill Motel - Deluxe Two Queens
1 bedroom, 2 queen beds, 1 bathroom
25–30 Sept
5.0 out of 5 average rating, 19 reviews
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Guest suite in Shaftsbury
Velvet Antlers Vintage Vermont Studio
1 bedroom, 2 beds, 1 bathroom
19–24 Oct
4.98 out of 5 average rating, 58 reviews
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Farm stay in Bennington
The Farm Cottage- Quiet 1BR on Hobby Farm
1 bedroom, 2 beds, 1 bathroom
18–23 Oct
4.98 out of 5 average rating, 264 reviews
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Cottage in Woodford
Willow Tree Cottage on Peaceful Mountain Lake
2 bedrooms, 3 beds, 1 bathroom
20–25 Oct
4.98 out of 5 average rating, 91 reviews
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Flat in Bennington
Cooper's Place
1 bedroom, 1 queen bed, 1 bathroom
20–25 Sept
4.95 out of 5 average rating, 196 reviews
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Hotel in Woodford
Welcome to Woodford Rest Suite 5!
2 bedrooms, 1 single bed, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 5 reviews
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Home in Shaftsbury
Converted Vermont Barn on 6.5 acres with hot tub
4 bedrooms, 2 beds, 1 bathroom
26–31 Oct
4.94 out of 5 average rating, 159 reviews
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Guest house in Bennington
The Hubbell Barn in Bennington VT East Room
1 bedroom, 1 king bed, 1 bathroom
23–28 Sept
4.93 out of 5 average rating, 90 reviews
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Guest suite in North Bennington
Charming Private Suite • Walk to Village
1 bedroom, 2 beds, 1 bathroom
14–19 Oct
4.89 out of 5 average rating, 70 reviews
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Home in Pownal
Cozy Home in Pownal VT
2 bedrooms, 3 beds, 1 bathroom
26–31 Oct
4.99 out of 5 average rating, 79 reviews
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Home in Bennington
1865 Farmhouse: mountain, monument & meadow views
3 bedrooms, 4 beds, 1.5 bathrooms
15–20 Nov
4.97 out of 5 average rating, 34 reviews
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Room in Shaftsbury
A charming 1800s home in true Vermont style.
1 double bed, 2 bathrooms
16–21 Sept
5.0 out of 5 average rating, 6 reviews