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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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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
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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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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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 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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Guest favourite
Cabin in Sandgate
Log Cabin Near Manchester, Dorset and Arlington
4 bedrooms, 9 beds, 2 bathrooms
28 Sept – 3 Oct
4.95 out of 5 average rating, 60 reviews
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Guest favourite
Home in Dorset
Classic Vermont Home with Mountain Views.
3 bedrooms, 4 beds, 2 bathrooms
27 Sept – 2 Oct
4.73 out of 5 average rating, 11 reviews
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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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Top guest favourite
Home in Manchester
The (Manchester) Center of it all!
3 bedrooms, 4 beds, 2 bathrooms
26–31 Oct
4.97 out of 5 average rating, 92 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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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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Guest favourite
Home in Dorset
Renovated Dorset Village Retreat • On the Green
4 bedrooms, 4 beds, 3 bathrooms
20–25 Sept
5.0 out of 5 average rating, 5 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
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Guest favourite
Home in Dorset
Home in the Heart of Dorset Village
3 bedrooms, 3 beds, 3.5 bathrooms
23–28 Sept
4.97 out of 5 average rating, 91 reviews
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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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Cabin in Granville
Gorgeous, Secluded, Lakeside Lodge
4 bedrooms, 5 beds, 2 bathrooms
29 Sept – 4 Oct
4.83 out of 5 average rating, 127 reviews