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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
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
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
Cottage in Winchester
The Humblebee Cottage
New place to stay, 2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
Campsite in Winchester
Escape to our serene RV pad in Winchester, NH
1 bedroom, 1 bed, 1 bathroom
7–12 Jul
Top guest favourite
Rooms in Hinsdale
Country Retreat
4.94 out of 5 average rating, 54 reviews, 2 bedrooms, 3 queen beds, 1 bathroom
4–9 Jun
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
Top guest favourite
Cottage in Brattleboro
Forest Street Retreat Attached Guest House
4.98 out of 5 average rating, 131 reviews, 2 bedrooms, 2 beds, 1 bathroom
26–31 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
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
Flat in Vernon
Deck, Mountain Views: Colorful Retreat in Vernon!
4.89 out of 5 average rating, 27 reviews, 2 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
Top guest favourite
Flat in Brattleboro
Guest House @ 120
4.99 out of 5 average rating, 99 reviews, 1 bedroom, 1 bed, 1 bathroom
30 Aug – 4 Sept
Guest favourite
Cabin in Vernon
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
4.9 out of 5 average rating, 100 reviews, 1 bedroom, 2 beds, 1 bathroom
9–14 Aug
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
Superhost
Home in Richmond
Porcupine Hill Farm
5.0 out of 5 average rating, 5 reviews, 6 bedrooms, 8 beds, 2 bathrooms
11–16 Jul
Top guest favourite
Room in Brattleboro
Maple St Guest Rm, Twin Beds, Brattleboro VT
4.92 out of 5 average rating, 461 reviews, 2 single beds, 2 bathrooms
24–29 Aug
Superhost
Home in Guilford
Charming historic farmhouse at Tapalou Guilds Farm
2 bedrooms, 3 beds, 1.5 bathrooms
20–25 Jul
Top guest favourite
Home in Brattleboro
1840 cottage
4.95 out of 5 average rating, 22 reviews, 2 bedrooms, 2 beds, 2 bathrooms
24–29 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