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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, 127 reviews
Guest favourite
Farm stay in Rupert
White Doe Farm •Lovingly restored antique farmhome
4 bedrooms, 6 beds
13–18 Oct
4.95 out of 5 average rating, 116 reviews
Home in Rupert
Mtn-View Rupert Village Home on Private Acreage
4 bedrooms, 7 beds
3–8 Sept
Top guest favourite
Farm stay in Dorset
Pond House... on a farm, by a pond
2 bedrooms, 3 beds
1–6 Nov
5.0 out of 5 average rating, 90 reviews
Top guest favourite
Guest suite in Dorset
Guest Suite in historic 1804 tavern, w/ Breakfast.
1 bedroom, 1 double bed
10–15 Sept
4.91 out of 5 average rating, 218 reviews
Superhost
Farm stay in Rupert
Sykes Hollow Farm- book your own private vt farm!
3 bedrooms, 4 beds
22–27 Oct
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Dorset
Charming Heart of Dorset Village 4 Season Retreat
3 bedrooms, 4 beds
20–25 Sept
4.93 out of 5 average rating, 46 reviews
Top guest favourite
Cottage in Sandgate
Historical, Equestrian Oronacah cottage rental
3 bedrooms, 4 beds
25–30 Oct
4.95 out of 5 average rating, 197 reviews
Guest favourite
Home in Pawlet
Vermont Getaway: Amazing Views, Hot Tub, & Sauna
5 bedrooms, 10 beds
2–7 Sept
4.96 out of 5 average rating, 55 reviews
Guest favourite
Home in Manchester
Ski and Play in Manchester Center!
5 bedrooms, 7 beds
6–11 Dec
4.95 out of 5 average rating, 136 reviews
Top guest favourite
Home in Mount Tabor
Cow Barn Lodge
5 bedrooms, 5 beds
2–7 Sept
4.98 out of 5 average rating, 295 reviews
Top guest favourite
Treehouse in Pawlet
Treehouse compound, no cleaning fee
4 bedrooms, 7 beds
7–12 Sept
4.97 out of 5 average rating, 143 reviews
Guest favourite
Cabin in Sandgate
Log Cabin Near Manchester, Dorset and Arlington
4 bedrooms, 9 beds
2–7 Sept
4.95 out of 5 average rating, 60 reviews
Top guest favourite
Cottage in Pawlet
Pond Cottage at Consider Bardwell Farm
2 bedrooms, 6 beds
13–18 Sept
4.94 out of 5 average rating, 110 reviews
Top guest favourite
Townhouse in Danby
Disconnect! Come Indulge in Nature- Spacious Home
3 bedrooms, 4 beds
3–8 Sept
5.0 out of 5 average rating, 68 reviews
Guest favourite
Cabin in Pawlet
Hickory Ridge, Vermont Log Cabin, no cleaning fee
2 bedrooms, 4 beds
6–11 Sept
4.93 out of 5 average rating, 187 reviews
Top guest favourite
Home in Dorset
Home in the Heart of Dorset Village
3 bedrooms, 3 beds
8–13 Sept
4.99 out of 5 average rating, 90 reviews
Barn in Dorset
The Carriage Barn: mountain views & walk to Dorset
2 bedrooms, 3 beds
2–7 Sept
New place to stay
Top guest favourite
Home in Fort Edward
Willow Creek Farm
4 bedrooms, 6 beds
16–21 Sept
4.96 out of 5 average rating, 26 reviews