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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
Cabin in Winchester
The Ironclad Mountain Retreat
2 bedrooms, 2 beds, 1 bathroom
4–9 Oct
4.83 out of 5 average rating, 60 reviews
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Guest favourite
Cottage in Winchester
The Humblebee Cottage
2 bedrooms, 3 beds, 1 bathroom
27 Sept – 2 Oct
4.9 out of 5 average rating, 10 reviews
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Guest favourite
Home in Richmond
Porcupine Hill Farm
6 bedrooms, 8 beds, 2 bathrooms
29 Sept – 4 Oct
5.0 out of 5 average rating, 9 reviews
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Guest favourite
Home in Guilford
Cozy Private Cabin in the Woods • Hemlock Haven
2 bedrooms, 3 beds, 1 bathroom
25–30 Oct
4.93 out of 5 average rating, 15 reviews
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Top guest favourite
Flat in Vernon
Farm land view.
1 bedroom, 1 queen bed, 1 bathroom
12–17 Oct
4.95 out of 5 average rating, 195 reviews
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Guest favourite
Yurt in Putney
Serene Yurt Near the Best of Southern Vermont
1 bedroom, 1 bed, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 9 reviews
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Guest favourite
Home in Swanzey
Lake Front Cottage
2 bedrooms, 2 double beds, 1 bathroom
13–18 Feb
5.0 out of 5 average rating, 8 reviews
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Top guest favourite
Home in Keene
The Brick House on Washington Street
3 bedrooms, 4 beds, 1 bathroom
19–24 Oct
4.93 out of 5 average rating, 251 reviews
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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, 57 reviews
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Top guest favourite
Place to stay in Chesterfield
The Ultimate Romantic Getaway
1 bed, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 67 reviews
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Guest favourite
Flat in Hinsdale
Welcome to the Kilburn House!
6 beds, 1 bathroom
9–14 Oct
5.0 out of 5 average rating, 6 reviews
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Top guest favourite
Bungalow in Brattleboro
Healix Vermont Getaway
1 bedroom, 4 beds, 1 bathroom
20–25 Nov
4.94 out of 5 average rating, 282 reviews
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Guest favourite
Tiny home in Chesterfield
Cozy Cottage on Spofford Lake
1 bedroom, 2 beds, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 7 reviews
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Top guest favourite
Flat in Marlboro
Shakespeare’s Folly Side Farm and AirBnB.
1 bedroom, 1 queen bed, 1 bathroom
17–22 Oct
4.93 out of 5 average rating, 311 reviews
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Top guest favourite
Home in New Salem
Stone n' Sky Lodge
5 bedrooms, 7 beds, 3 bathrooms
27 Oct – 1 Nov
4.91 out of 5 average rating, 254 reviews
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Guest favourite
Cabin in Brattleboro
Log Cabin on Maple Sugar Farm
4 bedrooms, 5 beds, 2.5 bathrooms
23–28 Sept
4.91 out of 5 average rating, 32 reviews
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Home in Chesterfield
Large Vacation Rental Nestled in 400 Acres
7 bedrooms, 14 single beds, 4 bathrooms
27 Sept – 2 Oct
New place to stay
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Guest favourite
Flat in Greenfield
Treetop Haven
2 bedrooms, 3 beds, 1 bathroom
25–30 Oct
4.92 out of 5 average rating, 51 reviews