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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, 3 bathrooms
13–18 Oct
4.95 out of 5 average rating, 117 reviews
Home in Rupert
Mtn-View Rupert Village Home on Private Acreage
4 bedrooms, 7 beds, 2.5 bathrooms
18–23 Oct
Top guest favourite
Farm stay in Dorset
Pond House... on a farm, by a pond
2 bedrooms, 3 beds, 1 bathroom
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, 1 bathroom
10–15 Sept
4.91 out of 5 average rating, 220 reviews
Guest favourite
Cabin in Sandgate
Log Cabin Near Manchester, Dorset and Arlington
4 bedrooms, 9 beds, 2 bathrooms
7–12 Sept
4.95 out of 5 average rating, 60 reviews
Top guest favourite
Cottage in Sandgate
Historical, Equestrian Oronacah cottage rental
3 bedrooms, 4 beds, 2 bathrooms
25–30 Oct
4.95 out of 5 average rating, 197 reviews
Superhost
Farm stay in Rupert
Sykes Hollow Farm- book your own private vt farm!
3 bedrooms, 4 beds, 2 bathrooms
22–27 Oct
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Cottage in Manchester
Edelweiss Cottage, Manchester VT
3 bedrooms, 5 beds, 2 bathrooms
18–23 Oct
4.99 out of 5 average rating, 109 reviews
Top guest favourite
Treehouse in Pawlet
Treehouse compound, no cleaning fee
4 bedrooms, 7 beds, 2 bathrooms
8–13 Sept
4.97 out of 5 average rating, 143 reviews
Top guest favourite
Home in Manchester
The (Manchester) Center of it all!
3 bedrooms, 4 beds, 2 bathrooms
20–25 Oct
4.97 out of 5 average rating, 92 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
Guest favourite
Home in Dorset
The Perfect Vermont Experience
4 bedrooms, 5 beds, 3 bathrooms
14–19 Sept
5.0 out of 5 average rating, 19 reviews
Guest favourite
Home in Manchester
Ski and Play in Manchester Center!
5 bedrooms, 7 beds, 2 bathrooms
6–11 Dec
4.95 out of 5 average rating, 136 reviews
Top guest favourite
Home in Dorset
Welcome to "Bumblinn" ~ Historic Dorset, VT
4 bedrooms, 5 beds, 2 bathrooms
22–27 Sept
5.0 out of 5 average rating, 26 reviews
Top guest favourite
Home in Mount Tabor
Cow Barn Lodge
5 bedrooms, 5 beds, 2.5 bathrooms
14–19 Sept
4.98 out of 5 average rating, 295 reviews
Guest favourite
Home in Dorset
Hot Tub Hideaway close to town
4 bedrooms, 4 beds, 2 bathrooms
1–6 Nov
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Dorset
Idyllic Dorset Home: Serene Escape w/amazing views
4 bedrooms, 5 beds, 3 bathrooms
21–26 Sept
4.98 out of 5 average rating, 41 reviews
Top guest favourite
Home in Dorset
Home in the Heart of Dorset Village
3 bedrooms, 3 beds, 3.5 bathrooms
11–16 Sept
4.99 out of 5 average rating, 90 reviews