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Search results; Over 1,000 homes in Winchester

Superhost
Guest house in Winchester
The Higgle House: A Sweetwater Farm Stay
2 bedrooms, 2 beds, 1 private bathroom
27 Jul – 1 Aug
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4.87 out of 5 average rating, 90 reviews
Superhost
Flat in Winchester
The Beam House | Cozy Rustic Retreat in Winchester
4.91 out of 5 average rating, 22 reviews, 1 bedroom, 2 beds, 1 bathroom
12–17 Jul
Guest favourite
Cabin in Winchester
The Ironclad Mountain Retreat
4.85 out of 5 average rating, 55 reviews, 2 bedrooms, 2 beds, 1 bathroom
27 Jul – 1 Aug
Cottage in Winchester
The Humblebee Cottage
New place to stay, 2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
Top guest favourite
Flat in Vernon
Farm land view.
4.95 out of 5 average rating, 190 reviews, 1 bedroom, 1 bed, 1 bathroom
14–19 Jul
Campsite in Winchester
Escape to our serene RV pad in Winchester, NH
1 bedroom, 1 bed, 1 bathroom
8–13 Jul
Top guest favourite
Room in Chesterfield
Peaceful Poet’s Farm
5.0 out of 5 average rating, 34 reviews, 1 bed, 1 bathroom
8–13 Jul
Guest favourite
Loft in Vernon
Studio w/ Trail Access ~ 10 Mi to Brattleboro!
4.92 out of 5 average rating, 26 reviews, 1 bed, 1 bathroom
13–18 Jul
Top guest favourite
Cabin in Guilford
Cozy Loft Cabin in Vermont with Sauna
5.0 out of 5 average rating, 29 reviews, 3 bedrooms, 7 beds, 1 bathroom
14–19 Jul
Guest favourite
Home in Guilford
Cozy Private Cabin in the Woods • Hemlock Haven
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 3 beds, 1 bathroom
31 Aug – 5 Sept
Guest favourite
Home in Richmond
Porcupine Hill Farm
5.0 out of 5 average rating, 5 reviews, 6 bedrooms, 8 beds, 2 bathrooms
11–16 Jul
Superhost
Home in Guilford
Charming historic farmhouse at Tapalou Guilds Farm
2 bedrooms, 3 beds, 1.5 bathrooms
20–25 Jul
Top guest favourite
Cabin in Brattleboro
Cottage
4.89 out of 5 average rating, 526 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul
Flat in Chesterfield
Lake-View Spofford Apartment w/ Shared Dock!
1 bedroom, 2 beds, 1 bathroom
10–15 Aug
Guest favourite
Home in Chesterfield
Governer's Brook Camp - 2 Bedroom
4.9 out of 5 average rating, 136 reviews, 2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
Top guest favourite
Tiny home in Brattleboro
Sweet Vermont Tiny Home Get Away
4.86 out of 5 average rating, 263 reviews, 1 bedroom, 1 bed, 1 bathroom
24–29 Aug
Guest favourite
Flat in Brattleboro
On the Water at North Bridge Cove, Patio and Sauna
4.96 out of 5 average rating, 67 reviews, 1 bedroom, 1 bed, 1 bathroom
8–13 Jul
Guest favourite
Flat in Greenfield
Treetop Haven
4.92 out of 5 average rating, 24 reviews, 2 bedrooms, 3 beds, 1 bathroom
9–14 Nov
Guest favourite
Tiny home in Brattleboro
“Elm” Cozy Pond-side Cabin w/wood stove
4.93 out of 5 average rating, 127 reviews, 1 bedroom, 2 beds, 1 bathroom
21–26 Aug