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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
4.83 out of 5 average rating, 60 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, 167 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, 9 reviews
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Home in Chesterfield
Large Vacation Rental Nestled in 400 Acres
7 bedrooms, 14 single beds, 4 bathrooms
1–6 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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Top guest favourite
Flat in Vernon
Farm land view.
1 bedroom, 1 queen bed, 1 bathroom
1–6 Oct
4.95 out of 5 average rating, 195 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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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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Guest favourite
Home in Marlborough
4 BR Monadnock View Luxury Chalet
4 bedrooms, 5 beds, 5.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 25 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
1–6 Oct
4.98 out of 5 average rating, 46 reviews
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Top guest favourite
Home in Putney
Charming Putney Village Home!
4 bedrooms, 7 beds, 2 bathrooms
26–31 Oct
4.95 out of 5 average rating, 22 reviews
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Top guest favourite
Place to stay in Chesterfield
The Ultimate Romantic Getaway
1 bed, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 67 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
Flat in Brattleboro
Quiet St in Town, gardens, terrace
1 bedroom, 2 beds, 1 bathroom
28 Oct – 2 Nov
4.9 out of 5 average rating, 423 reviews
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Top guest favourite
Treehouse in Guilford
Cozy tent in the trees on organic flower farm
1 bedroom, 1 king bed, WC
4–9 Oct
4.99 out of 5 average rating, 209 reviews
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Guest favourite
Flat in Dummerston
1850’s Barn Retreat
2 bedrooms, 2 beds, 1 bathroom
26–31 Oct
4.91 out of 5 average rating, 515 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