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Search results; Over 1,000 homes in Bennington

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, 123 reviews
Top guest favourite
Cottage in Shaftsbury
Rollin Cottage
2 bedrooms, 2 queen beds
27 Oct – 1 Nov
4.97 out of 5 average rating, 176 reviews
Top guest favourite
Home in Bennington
Cozy Mountain Retreat - Museums, Trails & Colleges
2 bedrooms, 3 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Arlington
Charming Vermont Retreat
5 bedrooms, 8 beds
14–19 Sept
5.0 out of 5 average rating, 31 reviews
Top guest favourite
Cabin in Woodford
Cozy, welcoming, Cabin in the woods!
3 bedrooms, 4 beds
19–24 Oct
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Guest suite in Shaftsbury
Velvet Antlers Vintage Vermont Studio
1 bedroom, 2 beds
19–24 Oct
4.98 out of 5 average rating, 58 reviews
Guest favourite
Home in Bennington
NEW Vermont Getaway- 2 blocks from SVMC, downtown
3 bedrooms, 3 queen beds
5–10 Oct
4.91 out of 5 average rating, 22 reviews
Top guest favourite
Home in Arlington
Mountain View Manor
4 bedrooms, 7 beds
19–24 Oct
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Home in Pownal
Cozy Home in Pownal VT
2 bedrooms, 3 beds
26–31 Oct
4.99 out of 5 average rating, 79 reviews
Top guest favourite
Home in Bennington
Cozy Modern Sugar House with spectacular views.
2 bedrooms, 3 beds
25–30 Oct
4.99 out of 5 average rating, 357 reviews
Top guest favourite
Home in Pownal
The Barn @ Blackberry Steep
4 bedrooms, 10 beds
14–19 Sept
5.0 out of 5 average rating, 15 reviews
Guest favourite
Home in Arlington
Southern Vermont Cottage
3 bedrooms, 5 beds
27 Sept – 2 Oct
4.93 out of 5 average rating, 137 reviews
Top guest favourite
Home in Shaftsbury
3-bedroom country home with mountain views
3 bedrooms, 4 beds
20–25 Sept
4.99 out of 5 average rating, 68 reviews
Guest favourite
Boutique hotel in Bennington
Harwood Hill Motel - Deluxe Two Queens
1 bedroom, 2 queen beds
25–30 Sept
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Cottage in Woodford
HoneyBear Lake Cottage
3 bedrooms, 4 beds
14–19 Sept
4.96 out of 5 average rating, 49 reviews
Top guest favourite
Cottage in Woodford
Willow Tree Cottage on Peaceful Mountain Lake
2 bedrooms, 3 beds
20–25 Oct
4.98 out of 5 average rating, 91 reviews
Guest favourite
Flat in Bennington
Cozy Loft steps from VT Downtown
1 bedroom, 1 queen bed
24–29 Sept
4.93 out of 5 average rating, 107 reviews
Guest favourite
Guest house in Bennington
The Hubbell Barn in Bennington VT East Room
1 bedroom, 1 king bed
23–28 Sept
4.93 out of 5 average rating, 90 reviews
Guest favourite
Home in Pownal
Brand-new private 3 - bedroom mtn retreat.
3 bedrooms, 2 beds
14–19 Sept
5.0 out of 5 average rating, 5 reviews