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Search results; Over 1,000 homes in Winchester

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Superhost
Guest house in Winchester
The Higgle House: A Sweetwater Farm Stay
2 bedrooms, 2 beds, 1 private bathroom
1–6 Nov
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4.86 out of 5 average rating, 92 reviews
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Guest favourite
Cottage in Winchester
The Humblebee Cottage
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.9 out of 5 average rating, 10 reviews
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Guest favourite
Cabin in Winchester
The Ironclad Mountain Retreat
2 bedrooms, 2 beds
4–9 Oct
4.83 out of 5 average rating, 60 reviews
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Guest favourite
Home in Richmond
Porcupine Hill Farm
6 bedrooms, 8 beds
29 Sept – 4 Oct
5.0 out of 5 average rating, 9 reviews
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Top guest favourite
Home in Putney
Charming Putney Village Home!
4 bedrooms, 7 beds
26 Sept – 1 Oct
4.95 out of 5 average rating, 21 reviews
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Home in Royalston
Historic Home w/ Modern Updates on < 4 Acres
4 bedrooms, 5 beds
27 Sept – 2 Oct
4.94 out of 5 average rating, 77 reviews
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Top guest favourite
Home in Keene
The Brick House on Washington Street
3 bedrooms, 4 beds
19–24 Oct
4.93 out of 5 average rating, 251 reviews
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Guest favourite
Home in West Brattleboro
Private Brookside Farmhouse
3 bedrooms, 4 beds
26 Sept – 1 Oct
4.93 out of 5 average rating, 88 reviews
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Top guest favourite
Cabin in West Brattleboro
Hidden Forest Cabin: Kitchen, Deck, Babbling Brook
3 bedrooms, 6 beds
27 Sept – 2 Oct
4.98 out of 5 average rating, 46 reviews
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Guest favourite
Home in Chesterfield
Governer's Brook Camp - 2 Bedroom
2 bedrooms, 3 beds
21–26 Sept
4.9 out of 5 average rating, 146 reviews
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Guest favourite
Home in Brattleboro
Bright, spacious country home
4 bedrooms, 5 beds
18–23 Oct
4.91 out of 5 average rating, 67 reviews
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Top guest favourite
Flat in Brattleboro
Charming 2BR Vermont Home • Porch • Full Kitchen
2 bedrooms, 3 beds
25–30 Oct
5.0 out of 5 average rating, 17 reviews
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Guest favourite
Flat in Swanzey
Swanzey Retreat-serene yet close to Keene
2 bedrooms, 2 beds
26–31 Oct
4.88 out of 5 average rating, 17 reviews
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Guest favourite
Home in Dummerston
Dutton Farmhouse
4 bedrooms, 6 beds
2–7 Nov
4.97 out of 5 average rating, 58 reviews
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Guest favourite
Cottage in Orange
The Film Shack: A Sweetwater Stay
5 bedrooms, 6 beds
26 Sept – 1 Oct
4.9 out of 5 average rating, 156 reviews
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Top guest favourite
Treehouse in Guilford
Cozy tent in the trees on organic flower farm
1 bedroom, 1 king bed
27 Sept – 2 Oct
4.99 out of 5 average rating, 209 reviews
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Top guest favourite
Yurt in Dover
Mount Snow Yurt: Hot Tub~Wood Stove~WiFi~EVcharger
3 bedrooms, 4 beds
26 Sept – 1 Oct
4.93 out of 5 average rating, 137 reviews
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Top guest favourite
Cottage in Orange
Lake House with view of mountain
2 bedrooms, 3 beds
20–25 May
4.99 out of 5 average rating, 96 reviews
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Guest favourite
Home in Chesterfield
Beautiful Home near the sand at Spofford Lake!
2 bedrooms, 6 beds
6–11 Oct
5.0 out of 5 average rating, 19 reviews