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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
Chalet in Winchester
Chalet Sonsie: A Sweetwater Stay
2 bedrooms, 3 beds, 1.5 bathrooms
3–8 Nov
4.85 out of 5 average rating, 168 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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Room in Northfield
Sturbridge Queen Room at Centennial House B&B
1 queen bed, 1 bathroom
25–30 Oct
New place to stay
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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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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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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
1–6 Nov
4.95 out of 5 average rating, 196 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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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
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
Flat in Brattleboro
Bright Garden View Apartment
1 bedroom, 1 queen bed, 1 bathroom
18–23 Oct
4.99 out of 5 average rating, 212 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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Top guest favourite
Cottage in Jaffrey
The Boathouse - A rustic and cozy lakeside cottage
1 bedroom, 4 beds, 1 bathroom
1–6 Oct
4.96 out of 5 average rating, 52 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
Cabin in Vernon
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
1 bedroom, 2 beds, 1 bathroom
11–16 Oct
4.9 out of 5 average rating, 104 reviews