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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, 129 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, 118 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
5.0 out of 5 average rating, 3 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, 222 reviews
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Guest favourite
Cabin in Sandgate
Log Cabin Near Manchester, Dorset and Arlington
4 bedrooms, 9 beds, 2 bathrooms
1–6 Oct
4.95 out of 5 average rating, 60 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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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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Guest favourite
Home in Dorset
Classic Vermont Home with Mountain Views.
3 bedrooms, 4 beds, 2 bathrooms
11–16 Oct
4.73 out of 5 average rating, 11 reviews
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Barn in Dorset
The Carriage Barn: mountain views & walk to Dorset
2 bedrooms, 3 beds, 1.5 bathrooms
15–20 Oct
New place to stay
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Home in Dorset
Dorset home away from home
5 bedrooms, 6 beds, 4 bathrooms
4–9 Oct
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Home in Manchester
4 Bedroom Charm in the heart of Manchester Center
4 bedrooms, 8 beds, 2.5 bathrooms
1–6 Dec
New place to stay
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Guest favourite
Home in Dorset
Mountain Serenity
3 bedrooms, 5 beds, 2.5 bathrooms
21–26 Jan
4.9 out of 5 average rating, 29 reviews
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Yurt in Mount Holly
Secluded Yurt in Mount Holly
1 bedroom, 2 beds, 1 bathroom
1–6 Oct
New place to stay
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Guest favourite
Home in Dorset
Minutes from Vt. Summer Festival and Ski slops
3 bedrooms, 6 beds, 2 bathrooms
4–9 Oct
4.95 out of 5 average rating, 37 reviews
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Tiny home in Wells
Mountain Top Getaway A-frame
1 bedroom, 3 beds, 1 bathroom
11–16 Oct
New place to stay
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Guest favourite
Home in Dorset
Renovated Dorset Village Retreat • On the Green
4 bedrooms, 4 beds, 3 bathrooms
12–17 Oct
5.0 out of 5 average rating, 5 reviews
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Superhost
Home in Dorset
Peaceful Vermont Farmhouse Escape
4 bedrooms, 5 beds, 3 bathrooms
19–24 Oct
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Flat in Dorset
Vermont barn apartment
1 bed, 1 bathroom
14–19 Oct
4.99 out of 5 average rating, 196 reviews
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Guest favourite
Home in Whitehall
Well appointed lakehouse. Peaceful family fun.
3 bedrooms, 5 beds, 2.5 bathrooms
4–9 Oct
4.86 out of 5 average rating, 271 reviews