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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
28 Aug – 2 Sept
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4.87 out of 5 average rating, 91 reviews
Superhost
Cabin in Winchester
The Ironclad Mountain Retreat
2 bedrooms, 2 beds, 1 bathroom
6–11 Aug
4.82 out of 5 average rating, 57 reviews
Superhost
Flat in Winchester
The Beam House | Cozy Rustic Retreat in Winchester
1 bedroom, 2 beds, 1 bathroom
2–7 Aug
4.92 out of 5 average rating, 24 reviews
Guest favourite
Cottage in Winchester
The Humblebee Cottage
2 bedrooms, 3 beds, 1 bathroom
9–14 Aug
4.86 out of 5 average rating, 7 reviews
Top guest favourite
Rooms in Hinsdale
Country Retreat
2 bedrooms, 3 queen beds, 1 bathroom
4–9 Jun
4.95 out of 5 average rating, 56 reviews
Guest favourite
Cabin in Vernon
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
1 bedroom, 2 beds, 1 bathroom
9–14 Aug
4.9 out of 5 average rating, 100 reviews
Guest favourite
Flat in Swanzey
Swanzey Retreat-serene yet close to Keene
2 bedrooms, 2 beds, 1 bathroom
18–23 Aug
4.85 out of 5 average rating, 13 reviews
Flat in Sunderland
A COZY Apartment Close to UMASS
4 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
New place to stay
Superhost
Home in Chesterfield
Peaceful and Private Farmhouse Retreat
3 bedrooms, 4 beds, 2 bathrooms
12–17 Aug
Guest favourite
Flat in Greenfield
Treetop Haven
2 bedrooms, 3 beds, 1 bathroom
9–14 Nov
4.94 out of 5 average rating, 33 reviews
Top guest favourite
Cottage in Bernardston
Cozy, Quiet Cottage on Country rd 2 mil from I-91
2 bedrooms, 2 beds, 1 bathroom
9–14 Sept
4.87 out of 5 average rating, 365 reviews
Top guest favourite
Cottage in Brattleboro
Forest Street Retreat Attached Guest House
2 bedrooms, 2 queen beds, 1 bathroom
10–15 Sept
4.99 out of 5 average rating, 141 reviews
Top guest favourite
Cottage in Newfane
Cozy Vermont Antique Sugar House with Fireplace
2 bedrooms, 3 beds, 1 bathroom
17–22 Aug
4.99 out of 5 average rating, 292 reviews
Top guest favourite
Home in Charlemont
Stone Ridge Cottage
2 bedrooms, 3 beds, 1.5 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 37 reviews
Guest favourite
Flat in Dummerston
1850’s Barn Retreat
2 bedrooms, 2 beds, 1 bathroom
6–11 Sept
4.91 out of 5 average rating, 505 reviews
Top guest favourite
Flat in Vernon
Farm land view.
1 bedroom, 1 queen bed, 1 bathroom
14–19 Aug
4.95 out of 5 average rating, 192 reviews
Top guest favourite
Flat in Dublin
Private Dublin apartment nestled in the woods
1 bedroom, 1 queen bed, 1 bathroom
11–16 Sept
4.97 out of 5 average rating, 280 reviews
Guest favourite
Flat in Keene
The Murdock Suite @ The Large House
2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
4.95 out of 5 average rating, 77 reviews
Top guest favourite
Home in Chesterfield
Charming Country Home
2 bedrooms, 3 beds, 2 bathrooms
3–8 Oct
4.98 out of 5 average rating, 308 reviews