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Search results; Over 1,000 homes in Rupert

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, 128 reviews
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
Home in Rupert
Mtn-View Rupert Village Home on Private Acreage
4 bedrooms, 7 beds, 2.5 bathrooms
18–23 Oct
Guest favourite
Cabin in Sandgate
Log Cabin Near Manchester, Dorset and Arlington
4 bedrooms, 9 beds, 2 bathrooms
14–19 Sept
4.95 out of 5 average rating, 60 reviews
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, 220 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
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
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
Guest favourite
Home in Dorset
Renovated Dorset Village Retreat • On the Green
4 bedrooms, 4 beds, 3 bathrooms
14–19 Sept
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Dorset
Glorious Mountain View in Dorset
3 bedrooms, 4 beds, 2 bathrooms
21–26 Sept
4.88 out of 5 average rating, 24 reviews
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
Top guest favourite
Flat in Salem
Yellow Door Inn
2 bedrooms, 2 beds, 1 bathroom
18–23 Oct
4.98 out of 5 average rating, 126 reviews
Guest favourite
Cabin in Manchester
Dragonfly Cottage - Mountain View A-Frame
3 bedrooms, 8 beds, 1.5 bathrooms
20–25 Sept
4.94 out of 5 average rating, 90 reviews
Top guest favourite
Home in Sandgate
Secluded Mountain Chalet | 12 Acres, Pond, Views
3 bedrooms, 5 beds, 2 bathrooms
15–20 Sept
5.0 out of 5 average rating, 16 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
Home in Tinmouth
Charming Vermont Schoolhouse
1 bedroom, 2 beds, 1 bathroom
9–14 Nov
4.99 out of 5 average rating, 121 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
Home in Dorset
Charming Dorset Cottage Nestled in the Treetops
3 bedrooms, 3 beds, 2.5 bathrooms
20–25 Sept
Flat in Pawlet
Loft 404 - Peaceful Private Vermont Retreat
1 bedroom, 1 queen bed, 1 bathroom
21–26 Sept
4.97 out of 5 average rating, 32 reviews