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Search results; Over 1,000 homes in Bennington

Top guest favourite
Home in Bennington
Cozy Modern Sugar House with spectacular views.
2 bedrooms, 3 beds, 1.5 private bathrooms
25–30 Oct
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4.99 out of 5 average rating, 356 reviews
Top guest favourite
Guest suite in Shaftsbury
Velvet Antlers Vintage Vermont Studio
1 bedroom, 2 beds, 1 bathroom
1–6 Dec
4.98 out of 5 average rating, 57 reviews
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, 6 reviews
Top guest favourite
Farm stay in Bennington
White Rock Farm
5 bedrooms, 8 beds, 3 bathrooms
20–25 Oct
4.98 out of 5 average rating, 140 reviews
Top guest favourite
Flat in North Adams
The MoCA-Cabana: 2 bd + Sauna
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.99 out of 5 average rating, 149 reviews
Top guest favourite
Flat in Bennington
Vermont Downtown Oasis
2 bedrooms, 2 beds, 1 bathroom
1–6 Nov
4.99 out of 5 average rating, 92 reviews
Home in Pownal
Brand-new private 3 - bedroom mtn retreat.
3 bedrooms, 2 beds, 2 bathrooms
10–15 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Flat in Bennington
Cooper's Place
1 bedroom, 1 queen bed, 1 bathroom
19–24 Sept
4.95 out of 5 average rating, 195 reviews
Guest favourite
Flat in Bennington
Cozy Loft steps from VT Downtown
1 bedroom, 1 queen bed, 1 bathroom
19–24 Sept
4.92 out of 5 average rating, 106 reviews
Top guest favourite
Home in Shaftsbury
3-bedroom country home with mountain views
3 bedrooms, 4 beds, 1 bathroom
7–12 Sept
4.99 out of 5 average rating, 68 reviews
Top guest favourite
Cabin in Woodford
Cozy, welcoming, Cabin in the woods!
3 bedrooms, 4 beds, 2.5 bathrooms
9–14 Sept
5.0 out of 5 average rating, 11 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, 373 reviews
Top guest favourite
Flat in Bennington
Scenic Vermont Studio
1 bed, 1 bathroom
9–14 Sept
4.92 out of 5 average rating, 202 reviews
Top guest favourite
Farm stay in Bennington
The Farm Cottage- Quiet 1BR on Hobby Farm
1 bedroom, 2 beds, 1 bathroom
27 Oct – 1 Nov
4.98 out of 5 average rating, 261 reviews
Top guest favourite
Cottage in Bennington
Cozy, bright 3-bedroom Cottage with fireplace.
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
4.98 out of 5 average rating, 123 reviews
Top guest favourite
Home in Pownal
The Barn @ Blackberry Steep
4 bedrooms, 10 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 15 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, 78 reviews
Guest favourite
Home in Bennington
NEW Vermont Getaway- 2 blocks from SVMC, downtown
3 bedrooms, 3 queen beds, 2 bathrooms
7–12 Sept
4.9 out of 5 average rating, 21 reviews
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, 89 reviews