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Search results; Over 1,000 homes in Winchester

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Guest favourite
Chalet in Winchester
Chalet Sonsie: A Sweetwater Stay
2 bedrooms, 3 beds, 1.5 shared bathrooms
3–8 Nov
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4.85 out of 5 average rating, 168 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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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
Flat in Vernon
Farm land view.
1 bedroom, 1 queen bed, 1 bathroom
21–26 Oct
4.95 out of 5 average rating, 196 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
Home in Northfield
Cozy Home with Relaxing Views
3 bedrooms, 3 beds, 1.5 bathrooms
1–8 Oct
4.88 out of 5 average rating, 32 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
Farm stay in Warwick
Be Still Meadows at Chase Hill Farm - first floor
1 bedroom, 2 beds, 1 bathroom
11–16 Oct
4.97 out of 5 average rating, 77 reviews
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Top guest favourite
Cabin in West Brattleboro
Hidden Forest Cabin: Kitchen, Deck, Babbling Brook
3 bedrooms, 6 beds, 1 bathroom
14–19 Oct
4.98 out of 5 average rating, 47 reviews
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Guest favourite
Place to stay in Winchendon
Enjoy your stay in an Antique Home in a Toy Museum
3 bedrooms, 3 beds, 2 bathrooms
1–6 Oct
4.9 out of 5 average rating, 106 reviews
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Guest favourite
Home in Brattleboro
Bright, spacious country home
4 bedrooms, 5 beds, 2 bathrooms
18–23 Oct
4.91 out of 5 average rating, 67 reviews
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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, 645 reviews
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Home in Charlemont
3 Bedroom 2 Bath Cottage on The Brook
3 bedrooms, 5 beds, 2 bathrooms
1–6 Oct
New place to stay
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Top guest favourite
Guest house in Chesterfield
House on a hill
1 bedroom, 1 bed, 1 bathroom
27 Oct – 1 Nov
4.98 out of 5 average rating, 116 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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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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Home in Chesterfield
Large Vacation Rental Nestled in 400 Acres
7 bedrooms, 14 single beds, 4 bathrooms
12–17 Oct
New place to stay