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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
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
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
Tower in Granville
Slateville Cabin & Tower equipped & secluded
2 bedrooms, 8 beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 58 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
Guest house in Salem
Guest House at Hummingbird Hill
1 bedroom, 2 queen beds, 1 bathroom
17–22 Sept
4.97 out of 5 average rating, 145 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
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
Home in Mount Tabor
Cow Barn Lodge
5 bedrooms, 5 beds, 2.5 bathrooms
1–6 Sept
4.99 out of 5 average rating, 292 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
Top guest favourite
Cottage in Sandgate
Iconic "Kreffer's Crossing" covered bridge cottage
2 bedrooms, 2 beds, 1 bathroom
21–26 Oct
4.99 out of 5 average rating, 79 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
Home in Wells
Relaxing Lakeside Cottage w/ Dock + EV charger
2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Cabin in Cambridge
Mountain View Glamping. Off-Grid & Dog Friendly
2 bedrooms, 2 queen beds, 1 bathroom
7–12 Sept
4.98 out of 5 average rating, 61 reviews
Top guest favourite
Home in Poultney
Waterfront Cabin • Dock • Fire Pit • Kayaks & SUPs
3 bedrooms, 5 beds, 1 bathroom
20–25 Sept
4.95 out of 5 average rating, 173 reviews
Top guest favourite
Flat in Manchester
Modern Vermont Retreat w/ Chef’s Kitchen
2 bedrooms, 2 beds, 1.5 bathrooms
26 Sept – 1 Oct
4.96 out of 5 average rating, 49 reviews