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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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Superhost
Flat in Winchester
The Beam House | Cozy Rustic Retreat in Winchester
1 bedroom, 2 beds, 1 bathroom
11–16 Oct
4.89 out of 5 average rating, 28 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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Rooms in Northfield
Deerfield King Suite at Centennial House B&B
2 bedrooms, 3 beds, 1 bathroom
25–30 Oct
New place to stay
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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
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
Home in Dummerston
Woodsy Retreat Near Skiing, Private Pool in Summer
2 bedrooms, 4 beds, 1.5 bathrooms
18–23 Oct
4.9 out of 5 average rating, 49 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
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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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
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
Cottage in Chesterfield
Tiny Cottage on Spofford Lake
1 bedroom, 1 queen bed, 1 bathroom
2–7 Oct
5.0 out of 5 average rating, 11 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
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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Home in Guilford
Writers Retreat! Peace and solitude.
1 bedroom, 1 queen bed, 1 bathroom
1–6 Oct
New place to stay