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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
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, 215 reviews
Home in Rupert
Mtn-View Rupert Village Home on Private Acreage
4 bedrooms, 7 beds, 2.5 bathrooms
22–27 Aug
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, 196 reviews
Top guest favourite
Cottage in Sandgate
Iconic "Kreffer's Crossing" covered bridge cottage
2 bedrooms, 2 beds, 1 bathroom
22–27 Aug
4.99 out of 5 average rating, 79 reviews
Top guest favourite
Cottage in Pawlet
The Smithy Cottage at Consider Bardwell Farm
2 beds, 1 bathroom
24–29 Aug
4.92 out of 5 average rating, 230 reviews
Flat in Pawlet
Loft 404 - Peaceful Private Vermont Retreat
1 bedroom, 1 queen bed, 1 bathroom
24–29 Aug
4.97 out of 5 average rating, 31 reviews
Top guest favourite
Cabin in Comstock
East Cabin
3 bedrooms, 6 beds, 2 bathrooms
4–9 Oct
4.98 out of 5 average rating, 174 reviews
Guest favourite
Tiny home in Granville
Gristmill Cabin overlooking peaceful brook.
1 bedroom, WC
23–28 Aug
4.95 out of 5 average rating, 148 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, 123 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
Guest favourite
Home in Dorset
Classic Vermont Home with Mountain Views.
3 bedrooms, 4 beds, 2 bathrooms
22–27 Aug
4.73 out of 5 average rating, 11 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
Top guest favourite
Treehouse in Jamaica
The Treehouse at Frog Pond Farm
1 bedroom, 2 beds, 1 bathroom
19–24 Oct
5.0 out of 5 average rating, 10 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, 212 reviews
Top guest favourite
Tiny home in Granville
Pond Cabin in Hebron.
1 queen bed, WC
23–28 Aug
4.96 out of 5 average rating, 134 reviews
Top guest favourite
Home in Wells
Relaxing Lakeside Cottage w/ Dock + EV charger
2 bedrooms, 2 beds, 1 bathroom
28 Aug – 2 Sept
5.0 out of 5 average rating, 18 reviews
Superhost
Cabin in Winhall
A frame cabin with Hot tub near Stratton, VT
2 bedrooms, 2 beds, 2 bathrooms
20–25 Sept
4.91 out of 5 average rating, 123 reviews
Top guest favourite
Cottage in Shaftsbury
Schoolhouse Spa Retreat on a Vermont Farm
2 bedrooms, 2 beds, 1 bathroom
8–13 Sept
4.98 out of 5 average rating, 777 reviews