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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, 217 reviews
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Home in Dorset
Renovated Dorset Village Retreat • On the Green
4 bedrooms, 4 beds, 3 bathrooms
1–6 Sept
5.0 out of 5 average rating, 4 reviews
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Home in Dorset
Glorious Mountain View in Dorset
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
4.87 out of 5 average rating, 23 reviews
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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
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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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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
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Home in Sandgate
Secluded Mountain Chalet | 12 Acres, Pond, Views
3 bedrooms, 5 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 16 reviews
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Bus in Granville
Serene Bus Getaway Among Rolling Farm Land
1 bedroom, 2 beds, 1 bathroom
13–18 Sept
4.89 out of 5 average rating, 215 reviews
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Cabin in Sandgate
Unique private retreat near fishing and hiking.
2 bedrooms, 4 beds, 1 bathroom
4–9 Feb
4.92 out of 5 average rating, 62 reviews
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Cabin in Manchester
Dragonfly Cottage - Mountain View A-Frame
3 bedrooms, 8 beds, 1.5 bathrooms
6–11 Sept
4.94 out of 5 average rating, 89 reviews
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Flat in Dorset
Newly Renovated Cottage
1 bedroom, 1 queen bed, 1 bathroom
13–18 Sept
4.82 out of 5 average rating, 91 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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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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Tiny home in Granville
Gristmill Cabin overlooking peaceful brook.
1 bedroom, WC
7–12 Sept
4.95 out of 5 average rating, 150 reviews
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Home in Manchester
Spacious Log Retreat, Minutes to Skiing, Sleeps 13
4 bedrooms, 10 beds, 3 bathrooms
2–7 Sept
New place to stay
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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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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