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Search results; Over 1,000 homes in Winchester

Superhost
Cabin in Winchester
Lakeside rustic seasonal cottage
2 bedrooms, 3 beds, 1 private bathroom
13–18 Sept
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4.83 out of 5 average rating, 36 reviews
Guest favourite
Cabin in Winchester
The Ironclad Mountain Retreat
2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
4.83 out of 5 average rating, 60 reviews
Guest favourite
Cottage in Winchester
The Humblebee Cottage
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
4.9 out of 5 average rating, 10 reviews
Top guest favourite
Cabin in Guilford
Cozy Loft Cabin in Vermont with Sauna
3 bedrooms, 7 beds, 1 bathroom
4–9 Sept
5.0 out of 5 average rating, 33 reviews
Guest favourite
Cabin in Vernon
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
1 bedroom, 2 beds, 1 bathroom
14–19 Sept
4.9 out of 5 average rating, 102 reviews
Top guest favourite
Flat in Vernon
Farm land view.
1 bedroom, 1 queen bed, 1 bathroom
22–27 Sept
4.95 out of 5 average rating, 193 reviews
Superhost
Home in Chesterfield
Peaceful and Private Farmhouse Retreat
3 bedrooms, 4 beds, 2 bathrooms
5–10 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Cottage in Bernardston
Cozy, Quiet Cottage on Country rd 2 mil from I-91
2 bedrooms, 2 beds, 1 bathroom
26–31 Oct
4.88 out of 5 average rating, 369 reviews
Guest favourite
Home in Guilford
Cozy Private Cabin in the Woods • Hemlock Haven
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.92 out of 5 average rating, 12 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, 315 reviews
Top guest favourite
Flat in Keene
The Murdock Suite @ The Large House
2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
4.95 out of 5 average rating, 80 reviews
Top guest favourite
Cottage in Brattleboro
Forest Street Retreat Attached Guest House
2 bedrooms, 2 queen beds, 1 bathroom
29 Oct – 3 Nov
4.99 out of 5 average rating, 146 reviews
Top guest favourite
Home in Brattleboro
1840 cottage
2 bedrooms, 2 beds, 2 bathrooms
12–17 Sept
4.96 out of 5 average rating, 27 reviews
Top guest favourite
Cabin in West Brattleboro
Hidden Forest Cabin: Kitchen, Deck, Babbling Brook
3 bedrooms, 6 beds, 1 bathroom
4–9 Sept
4.98 out of 5 average rating, 46 reviews
Guest favourite
Flat in Montague
Beautifully renovated three bedroom
3 bedrooms, 3 beds, 2 bathrooms
28 Oct – 2 Nov
4.91 out of 5 average rating, 499 reviews
Guest favourite
Flat in Swanzey
Swanzey Retreat-serene yet close to Keene
2 bedrooms, 2 beds, 1 bathroom
26–31 Oct
4.88 out of 5 average rating, 16 reviews
Guest favourite
Home in Dummerston
Woodsy Retreat Near Skiing, Private Pool in Summer
2 bedrooms, 4 beds, 1.5 bathrooms
13–18 Sept
4.89 out of 5 average rating, 45 reviews
Top guest favourite
Guest suite in Brattleboro
Charming studio in renovated 19th century church.
2 beds, 1 bathroom
1–6 Nov
4.95 out of 5 average rating, 641 reviews
Top guest favourite
Flat in Brattleboro
Apt in town 2 BR/2 levels in Victorian Farmhouse
2 bedrooms, 2 queen beds, 1 bathroom
19–24 Sept
4.95 out of 5 average rating, 350 reviews