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Search results; Over 1,000 homes in Rupert

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Guest favourite
Farm stay in Rupert
White Doe Farm •Lovingly restored antique farmhome
4 bedrooms, 6 beds, 3 bathrooms
27 Sept – 2 Oct
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4.95 out of 5 average rating, 115 reviews
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Home in Rupert
Mtn-View Rupert Village Home on Private Acreage
4 bedrooms, 7 beds, 2.5 bathrooms
1–6 Sept
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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, 216 reviews
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Cabin in Rupert
Elegant & Rustic Cabin - A Peaceful VT Getaway.
4 bedrooms, 6 beds, 1 bathroom
9–14 Nov
4.99 out of 5 average rating, 127 reviews
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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
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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
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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
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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, 186 reviews
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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
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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
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Superhost
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
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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
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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, 110 reviews
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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
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Home in Dorset
Dorset home away from home
5 bedrooms, 6 beds, 4 bathrooms
9–14 Sept
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Home in Mount Tabor
Cow Barn Lodge
5 bedrooms, 5 beds, 2.5 bathrooms
1–6 Sept
4.98 out of 5 average rating, 294 reviews
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Apartment in Dorset
Dorset, Vermont mountain retreat
2 bedrooms, 2 queen beds, 2.5 bathrooms
11–16 Sept
5.0 out of 5 average rating, 16 reviews
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Home in Salem
Magical Farm Getaway - a must visit!
5 bedrooms, 10 beds, 2.5 bathrooms
13–18 Sept
4.98 out of 5 average rating, 212 reviews
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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, 50 reviews