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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, 167 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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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
Home in Northfield
Cozy Home with Relaxing Views
3 bedrooms, 3 beds, 1.5 bathrooms
20–27 Sept
4.88 out of 5 average rating, 32 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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Rooms in Northfield
Deerfield King Suite at Centennial House B&B
2 bedrooms, 3 beds, 1 bathroom
20–25 Sept
New place to stay
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Top guest favourite
Cottage in Orange
Lake House with view of mountain
2 bedrooms, 3 beds, 1 bathroom
20–25 May
4.99 out of 5 average rating, 96 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
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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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
Flat in Brattleboro
Charming 2BR Vermont Home • Porch • Full Kitchen
2 bedrooms, 3 beds, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 17 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
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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Guest favourite
Home in Chesterfield
Beautiful Home near the sand at Spofford Lake!
2 bedrooms, 6 beds, 2 bathrooms
6–11 Oct
5.0 out of 5 average rating, 19 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, 644 reviews
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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
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Top guest favourite
Cabin in West Brattleboro
Hidden Forest Cabin: Kitchen, Deck, Babbling Brook
3 bedrooms, 6 beds, 1 bathroom
27 Sept – 2 Oct
4.98 out of 5 average rating, 46 reviews