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Search results; Over 1,000 homes in Rupert

Guest favourite
Farm stay in Rupert
White Doe Farm •Lovingly restored antique farmhome
4 bedrooms, 6 beds, 3 bathrooms
13–18 Oct
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4.95 out of 5 average rating, 117 reviews
Home in Rupert
Mtn-View Rupert Village Home on Private Acreage
4 bedrooms, 7 beds, 2.5 bathrooms
18–23 Oct
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, 90 reviews
Top guest favourite
Guest suite in Dorset
Guest Suite in historic 1804 tavern, w/ Breakfast.
1 bedroom, 1 double bed, 1 bathroom
11–16 Sept
4.91 out of 5 average rating, 220 reviews
Top guest favourite
Cabin in Rupert
Elegant & Rustic Cabin - A Peaceful VT Getaway.
4 bedrooms, 6 beds, 1 bathroom
9–14 Nov
4.99 out of 5 average rating, 128 reviews
Top guest favourite
Treehouse in Pawlet
Treehouse compound, no cleaning fee
4 bedrooms, 7 beds, 2 bathrooms
13–18 Sept
4.97 out of 5 average rating, 144 reviews
Guest favourite
Home in Dorset
Renovated Dorset Village Retreat • On the Green
4 bedrooms, 4 beds, 3 bathrooms
11–16 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Manchester
The (Manchester) Center of it all!
3 bedrooms, 4 beds, 2 bathrooms
21–26 Sept
4.97 out of 5 average rating, 92 reviews
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
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, 197 reviews
Guest favourite
Home in Dorset
Minutes from Vt. Summer Festival and Ski slops
3 bedrooms, 6 beds, 2 bathrooms
20–25 Sept
4.95 out of 5 average rating, 37 reviews
Guest favourite
Home in Dorset
Classic Vermont Home with Mountain Views.
3 bedrooms, 4 beds, 2 bathrooms
12–17 Sept
4.73 out of 5 average rating, 11 reviews
Guest favourite
Cabin in Sandgate
Log Cabin Near Manchester, Dorset and Arlington
4 bedrooms, 9 beds, 2 bathrooms
11–16 Sept
4.95 out of 5 average rating, 60 reviews
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
Flat in Manchester
Apartment in Manchester Center
3 bedrooms, 4 beds, 1 bathroom
21–26 Sept
New place to stay
Top guest favourite
Cottage in Manchester
Edelweiss Cottage, Manchester VT
3 bedrooms, 5 beds, 2 bathrooms
18–23 Oct
4.99 out of 5 average rating, 109 reviews
Guest favourite
Cabin in Pawlet
Hickory Ridge, Vermont Log Cabin, no cleaning fee
2 bedrooms, 4 beds, 4 bathrooms
13–18 Sept
4.93 out of 5 average rating, 187 reviews
Guest favourite
Home in Whitehall
Well appointed lakehouse. Peaceful family fun.
3 bedrooms, 5 beds, 2.5 bathrooms
19–24 Oct
4.86 out of 5 average rating, 271 reviews
Top guest favourite
Home in Mount Tabor
Cow Barn Lodge
5 bedrooms, 5 beds, 2.5 bathrooms
14–19 Sept
4.98 out of 5 average rating, 295 reviews