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Search results; Over 1,000 homes in Rupert

Top guest favourite
Cabin in Rupert
Elegant & Rustic Cabin - A Peaceful VT Getaway.
4 bedrooms, 6 beds, 1 private bathroom
9–14 Nov
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4.99 out of 5 average rating, 126 reviews
Home in Rupert
Mtn-View Rupert Village Home on Private Acreage
4 bedrooms, 7 beds, 2.5 bathrooms
1–6 Sept
Top guest favourite
Guest suite in Dorset
Guest Suite in historic 1804 tavern, w/ Breakfast.
1 bedroom, 1 double bed, 1 bathroom
5–10 Sept
4.91 out of 5 average rating, 216 reviews
Barn in Dorset
The Carriage Barn: mountain views & walk to Dorset
2 bedrooms, 3 beds, 1.5 bathrooms
1–6 Sept
New place to stay
Top guest favourite
Cottage in Sandgate
Historical, Equestrian Oronacah cottage rental
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
4.95 out of 5 average rating, 197 reviews
Top guest favourite
Treehouse in Pawlet
Treehouse compound, no cleaning fee
4 bedrooms, 7 beds, 2 bathrooms
7–12 Sept
4.96 out of 5 average rating, 142 reviews
Top guest favourite
Cottage in Pawlet
Pond Cottage at Consider Bardwell Farm
2 bedrooms, 6 beds, 1 bathroom
13–18 Sept
4.94 out of 5 average rating, 109 reviews
Top guest favourite
Barn in Manchester
Cozy Barn home w/ Mountain Views
1 bedroom, 1 queen bed, 1 bathroom
8–13 Nov
4.98 out of 5 average rating, 124 reviews
Top guest favourite
Home in Dorset
Charming Heart of Dorset Village 4 Season Retreat
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.93 out of 5 average rating, 46 reviews
Top guest favourite
Home in Dorset
Home in the Heart of Dorset Village
3 bedrooms, 3 beds, 3.5 bathrooms
8–13 Sept
4.99 out of 5 average rating, 89 reviews
Flat in Pawlet
Loft 404 - Peaceful Private Vermont Retreat
1 bedroom, 1 queen bed, 1 bathroom
7–12 Sept
4.97 out of 5 average rating, 31 reviews
Superhost
Home in Dorset
Newly renovated sparkling clean on Dorset West Rd
4 bedrooms, 6 beds, 2 bathrooms
1–6 Nov
New place to stay
Top guest favourite
Cabin in Granville
Mountain Cabin on 56 ac outdoor hot tub Hebron, NY
2 bedrooms, 10 beds, 2 bathrooms
3–8 Sept
4.96 out of 5 average rating, 128 reviews
Top guest favourite
Home in Dorset
Idyllic Dorset Home: Serene Escape w/amazing views
4 bedrooms, 5 beds, 3 bathrooms
6–11 Sept
4.97 out of 5 average rating, 39 reviews
Top guest favourite
Bus in Granville
Serene Bus Getaway Among Rolling Farm Land
1 bedroom, 2 beds, 1 bathroom
13–18 Sept
4.9 out of 5 average rating, 213 reviews
Top guest favourite
Cottage in Manchester
Edelweiss Cottage, Manchester VT
3 bedrooms, 5 beds, 2 bathrooms
12–17 Sept
4.99 out of 5 average rating, 107 reviews
Guest favourite
Cabin in Pawlet
Hickory Ridge, Vermont Log Cabin, no cleaning fee
2 bedrooms, 4 beds, 4 bathrooms
6–11 Sept
4.92 out of 5 average rating, 185 reviews
Top guest favourite
Apartment in Dorset
Dorset, Vermont mountain retreat
2 bedrooms, 2 queen beds, 2.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 16 reviews
Guest favourite
Home in Dorset
Classic Vermont Home with Mountain Views.
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
4.73 out of 5 average rating, 11 reviews