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Search results; Over 1,000 homes in Bennington

Top guest favourite
Cottage in Bennington
Historic Cottage • 140-Year Pool Table & Garden
3 bedrooms, 3 beds, 2 private bathrooms
24–29 Oct
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5.0 out of 5 average rating, 40 reviews
Top guest favourite
Home in Bennington
Cozy Mountain Retreat - Museums, Trails & Colleges
2 bedrooms, 3 beds, 1 bathroom
14–19 Sept
5.0 out of 5 average rating, 7 reviews
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, 356 reviews
Top guest favourite
Home in Bennington
Dreamy & stylish log cabin near town w/ fast wifi
2 bedrooms, 4 beds, 2 bathrooms
21–26 Sept
4.99 out of 5 average rating, 91 reviews
Top guest favourite
Guest suite in Shaftsbury
Velvet Antlers Vintage Vermont Studio
1 bedroom, 2 beds, 1 bathroom
22–27 Sept
4.98 out of 5 average rating, 58 reviews
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, 262 reviews
Top guest favourite
Cabin in Woodford
Cozy, welcoming, Cabin in the woods!
3 bedrooms, 4 beds, 2.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 11 reviews
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
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
Top guest favourite
Home in North Adams
Steps to MoCA private house + SAUNA!
4 bedrooms, 6 beds, 1 bathroom
20–25 Sept
4.98 out of 5 average rating, 559 reviews
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, 375 reviews
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
Top guest favourite
Home in Arlington
Charming Vermont Retreat
5 bedrooms, 8 beds, 3 bathrooms
13–18 Sept
5.0 out of 5 average rating, 31 reviews
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
Guest favourite
Home in Bennington
NEW Vermont Getaway- 2 blocks from SVMC, downtown
3 bedrooms, 3 queen beds, 2 bathrooms
11–16 Sept
4.9 out of 5 average rating, 21 reviews
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, 107 reviews
Top guest favourite
Guest suite in Shaftsbury
Peaceful get away at birds of a feather
2 beds, 1 bathroom
27 Sept – 2 Oct
4.98 out of 5 average rating, 191 reviews
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
Top guest favourite
Cottage in Woodford
HoneyBear Lake Cottage
3 bedrooms, 4 beds, 1.5 bathrooms
14–19 Sept
4.96 out of 5 average rating, 49 reviews