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Search results; Over 1,000 homes in Rupert

Top guest favorite
This West Rupert cabin sets you on 10 wooded acres with mountain views and a creek
4 bedrooms, 6 beds, 1 private bath
Aug 16 – 21
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4.99 out of 5 average rating, 125 reviews
Guest favorite
This renovated 1860s Rupert farmhouse gives you a fire pit, sun room, and 10 acres
4.95 out of 5 average rating, 115 reviews, 4 bedrooms, 6 beds, 3 baths
Aug 17 – 22
This 1806 Rupert home gives you a pro kitchen from PBS’s Cook’s Country
4 bedrooms, 7 beds, 2.5 baths
Aug 16 – 21
Top guest favorite
You’ll have the third floor of this 1804 Dorset tavern all to yourself
4.91 out of 5 average rating, 213 reviews, 1 bedroom, 1 bed, 1 bath
Aug 16 – 21
Guest favorite
This Dorset house gives you a hot tub, fire pit, and fireplace to come home to
4.92 out of 5 average rating, 26 reviews, 3 bedrooms, 5 beds, 2.5 baths
Dec 17 – 22
Guest favorite
This tiny Adirondacks cabin sits on 4 wooded acres where you’ll hear only birdsong
5.0 out of 5 average rating, 5 reviews, 1 bedroom, 1 bed, 1 bath
Sep 14 – 19
This hand-carved post and beam Shaftsbury house gives you mountain views on 10 acres
5.0 out of 5 average rating, 4 reviews, 2 bedrooms, 2 beds, 2 baths
Aug 17 – 22
Top guest favorite
This renovated 1850s post-and-beam guesthouse gives you 60 acres in the Adirondacks
4.91 out of 5 average rating, 1013 reviews, 1 bedroom, 2 beds, 1 bath
Aug 27 – Sep 1
Guest favorite
This secluded Sandgate guesthouse puts you on 8 acres along the Green River
4.96 out of 5 average rating, 28 reviews, 1 bedroom, 3 beds, 1 bath
Aug 23 – 28
Top guest favorite
This Hebron cabin sits on 56 acres where you’ll find a sauna, hot tub, and mountain views
4.96 out of 5 average rating, 127 reviews, 2 bedrooms, 10 beds, 2 baths
Aug 13 – 18
Top guest favorite
This newly built Manchester cabin gives you a loft bedroom, patio, and BBQ area
5.0 out of 5 average rating, 18 reviews, 1 bedroom, 1 bed, 1.5 baths
Aug 22 – 27
Top guest favorite
Mountain views and a hot tub greet you at this walkable Dorset village home
5.0 out of 5 average rating, 26 reviews, 4 bedrooms, 5 beds, 2 baths
Sep 22 – 27
Top guest favorite
This Hartford guesthouse gives you a private waterfall, trails, and 32 wooded acres
4.98 out of 5 average rating, 88 reviews, 2 bedrooms, 2 beds, 1 bath
Sep 13 – 18
Top guest favorite
This historic carriage house in Dorset gives you a pond, fireplace, and willow-lined drive
4.99 out of 5 average rating, 89 reviews, 3 bedrooms, 3 beds, 3.5 baths
Aug 17 – 22
Top guest favorite
Look out over the Green Mountains from this hillside Manchester cottage
4.99 out of 5 average rating, 107 reviews, 3 bedrooms, 5 beds, 2 baths
Sep 6 – 11
Top guest favorite
Stargaze from the hot tub at this wooded Adirondacks treehouse
4.99 out of 5 average rating, 128 reviews, 1 bedroom, 1 bed, 1 bath
Aug 16 – 21
Guest favorite
This creekside Dover yurt gives you a hot tub, cedar sauna, and glass dome
4.92 out of 5 average rating, 127 reviews, 3 bedrooms, 4 beds, 1.5 baths
Aug 18 – 23
Top guest favorite
This Sandgate cottage puts you on a 320-acre equestrian farm with lake access
4.95 out of 5 average rating, 194 reviews, 3 bedrooms, 4 beds, 2 baths
Sep 8 – 13
Top guest favorite
This lakefront Adirondacks home puts you on a private peninsula with kayaks and a dock
5.0 out of 5 average rating, 48 reviews, 2 bedrooms, 2 beds, 1 bath
Oct 19 – 24