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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
4.84 out of 5 average rating, 61 reviews
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Guest favourite
Cottage in Winchester
The Humblebee Cottage
2 bedrooms, 3 beds, 1 bathroom
17–22 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
1–6 Oct
5.0 out of 5 average rating, 10 reviews
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Top guest favourite
Place to stay in Chesterfield
The Ultimate Romantic Getaway
1 bed, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 67 reviews
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Home in Chesterfield
Large Vacation Rental Nestled in 400 Acres
7 bedrooms, 14 single beds, 4 bathrooms
12–17 Oct
New place to stay
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Top guest favourite
Flat in Vernon
Farm land view.
1 bedroom, 1 queen bed, 1 bathroom
1–6 Nov
4.95 out of 5 average rating, 196 reviews
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Superhost
Home in Chesterfield
Peaceful and Private Farmhouse Retreat
3 bedrooms, 4 beds, 2 bathrooms
21–26 Oct
5.0 out of 5 average rating, 3 reviews
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Superhost
Flat in Marlboro, Vermont
Shakespeare's Cherry Tree Cottage
1 bedroom, 2 queen beds, 1 bathroom
18–23 Oct
New place to stay
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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
Treehouse in Putney
Treehouse Haven in Putney-All Seasons
2 beds, 1 bathroom
18–23 Oct
4.97 out of 5 average rating, 203 reviews
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Guest favourite
Flat in Vernon
Deck, Mountain Views: Colorful Retreat in Vernon!
2 bedrooms, 3 beds, 2 bathrooms
25–30 Oct
4.86 out of 5 average rating, 35 reviews
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Guest favourite
Flat in Hinsdale
Welcome to the Kilburn House!
6 beds, 1 bathroom
16–21 Dec
5.0 out of 5 average rating, 6 reviews
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Guest favourite
Cottage in Chesterfield
Modern Luxury on the Lake
1 bedroom, 2 beds, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 6 reviews
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Guest favourite
Guest house in Brattleboro
Casita by the Green: Quiet, Country, close to town
1 bedroom, 2 beds, 1 bathroom
1–6 Oct
4.94 out of 5 average rating, 77 reviews
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Top 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
Cabin in Newfane
Log Cabin: Amazing Views, River Frontage, Hot Tub
2 bedrooms, 4 beds, 1 bathroom
8–13 Dec
4.99 out of 5 average rating, 320 reviews
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Top guest favourite
Guest suite in Jaffrey
Comfy Quarters Suite 1
1 bedroom, 2 beds, 1 bathroom
4–9 Oct
4.95 out of 5 average rating, 380 reviews
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Top guest favourite
Tiny home in Jamaica
Apple Blossom Cottage: A Tiny House
1 bedroom, 2 beds, 1 bathroom
8–13 Nov
4.94 out of 5 average rating, 1385 reviews