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Search results; Over 1,000 homes in Bennington

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Top guest favourite
Cottage in Bennington
Cozy, bright 3-bedroom Cottage with fireplace.
3 bedrooms, 4 beds, 2 private bathrooms
27 Sept – 2 Oct
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4.98 out of 5 average rating, 124 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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Top guest favourite
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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Top guest favourite
Home in Bennington
Cozy Modern Sugar House with spectacular views.
2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
4.99 out of 5 average rating, 357 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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Top guest favourite
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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Top guest favourite
Home in Bennington
Dreamy & stylish log cabin near town w/ fast wifi
2 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
4.99 out of 5 average rating, 91 reviews
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Top guest favourite
Home in Bennington
Southern Vermont Home
3 bedrooms, 3 queen beds, 1 bathroom
18–23 Oct
4.99 out of 5 average rating, 376 reviews
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Top guest favourite
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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Top guest favourite
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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Guest favourite
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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Top guest favourite
Cottage in Woodford
HoneyBear Lake Cottage
3 bedrooms, 4 beds, 1.5 bathrooms
22–27 Sept
4.96 out of 5 average rating, 49 reviews
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Home in Arlington
Charming Vermont Retreat
5 bedrooms, 8 beds, 3 bathrooms
16–21 Sept
5.0 out of 5 average rating, 31 reviews
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Top guest favourite
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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Guest favourite
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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Top guest favourite
Home in Shaftsbury
3-bedroom country home with mountain views
3 bedrooms, 4 beds, 1 bathroom
20–25 Sept
4.99 out of 5 average rating, 68 reviews
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Top guest favourite
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 favourite
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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Guest favourite
Home in Arlington
Southern Vermont Cottage
3 bedrooms, 5 beds, 2 bathrooms
27 Sept – 2 Oct
4.93 out of 5 average rating, 137 reviews