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Search results; Over 1,000 homes in Rupert

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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
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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, 218 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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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
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Cottage in Manchester
Edelweiss Cottage, Manchester VT
3 bedrooms, 5 beds, 2 bathrooms
12–17 Sept
4.99 out of 5 average rating, 108 reviews
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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, 90 reviews
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Treehouse in Pawlet
Treehouse compound, no cleaning fee
4 bedrooms, 7 beds, 2 bathrooms
7–12 Sept
4.97 out of 5 average rating, 143 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 Granville
Log Cabin near Lake George w/ Game Room & Hot Tub
2 bedrooms, 5 beds, 1 bathroom
7–12 Sept
4.91 out of 5 average rating, 23 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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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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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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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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Home in Dorset
Mountain Serenity
3 bedrooms, 5 beds, 2.5 bathrooms
17–22 Dec
4.89 out of 5 average rating, 28 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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Cabin in Sandgate
Log Cabin Near Manchester, Dorset and Arlington
4 bedrooms, 9 beds, 2 bathrooms
1–6 Sept
4.95 out of 5 average rating, 60 reviews