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Search results; Over 1,000 homes in Rupert

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Top guest favourite
Cabin in Rupert
Rustic & Elegant VT Cabin - A Peaceful Getaway
4 bedrooms, 6 beds, 1 private bathroom
2–7 Nov
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4.99 out of 5 average rating, 128 reviews
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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
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Home in Rupert
Mtn-View Rupert Village Home on Private Acreage
4 bedrooms, 7 beds, 2.5 bathrooms
18–23 Oct
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Guest favourite
Cabin in Sandgate
Log Cabin Near Manchester, Dorset and Arlington
4 bedrooms, 9 beds, 2 bathrooms
19–24 Sept
4.95 out of 5 average rating, 60 reviews
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Top guest favourite
Guest suite in Dorset
Guest Suite in historic 1804 tavern, w/ Breakfast.
1 bedroom, 1 double bed, 1 bathroom
18–23 Oct
4.91 out of 5 average rating, 221 reviews
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Top guest favourite
Home in Dorset
Charming Heart of Dorset Village 4 Season Retreat
3 bedrooms, 4 beds, 2 bathrooms
19–24 Oct
4.93 out of 5 average rating, 46 reviews
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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, 91 reviews
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Top guest favourite
Treehouse in Pawlet
Treehouse compound, no cleaning fee
4 bedrooms, 7 beds, 2 bathrooms
1–6 Jun
4.97 out of 5 average rating, 145 reviews
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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
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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, 198 reviews
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Guest favourite
Cabin in Pawlet
Hickory Ridge, Vermont Log Cabin, no cleaning fee
2 bedrooms, 4 beds, 4 bathrooms
26–31 Oct
4.93 out of 5 average rating, 187 reviews
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Guest favourite
Home in Dorset
The Perfect Vermont Experience
4 bedrooms, 5 beds, 3 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 19 reviews
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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
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Barn in Dorset
The Carriage Barn: mountain views & walk to Dorset
2 bedrooms, 3 beds, 1.5 bathrooms
19–24 Sept
New place to stay
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Superhost
Home in Dorset
Newly renovated sparkling clean on Dorset West Rd
4 bedrooms, 6 beds, 2 bathrooms
1–6 Nov
New place to stay
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Cabin in Wells
Mountaintop Getaway - Serenity Ridge
1 bedroom, 2 beds, WC
19–24 Sept
New place to stay
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Home in Dorset
Dorset home away from home
5 bedrooms, 6 beds, 4 bathrooms
21–26 Sept
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Home in Dorset
Charming Dorset Cottage Nestled in the Treetops
3 bedrooms, 3 beds, 2.5 bathrooms
20–25 Sept
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Guest favourite
Home in Pawlet
Vermont Getaway: Amazing Views, Hot Tub, & Sauna
5 bedrooms, 10 beds, 5.5 bathrooms
19–24 Sept
4.96 out of 5 average rating, 55 reviews