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Search results; Over 1,000 homes in Winchester

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Guest favourite
Cabin in Winchester
Lakeside rustic seasonal cottage
2 bedrooms, 3 beds, 1 private bathroom
13–18 Sept
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4.86 out of 5 average rating, 35 reviews
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Cottage in Winchester
The Humblebee Cottage
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
4.89 out of 5 average rating, 9 reviews
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Chalet in Winchester
Chalet Sonsie: A Sweetwater Stay
2 bedrooms, 3 beds, 1.5 bathrooms
16–21 Sept
4.85 out of 5 average rating, 165 reviews
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Cabin in Winchester
The Ironclad Mountain Retreat
2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
4.83 out of 5 average rating, 60 reviews
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Home in Richmond
Porcupine Hill Farm
6 bedrooms, 8 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 8 reviews
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Cabin in Guilford
Cozy Loft Cabin in Vermont with Sauna
3 bedrooms, 7 beds, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 33 reviews
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Home in Brattleboro
Bright, spacious country home
4 bedrooms, 5 beds, 2 bathrooms
1–6 Sept
4.92 out of 5 average rating, 64 reviews
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Home in Putney
Charming Putney Village Home!
4 bedrooms, 7 beds, 2 bathrooms
26 Sept – 1 Oct
4.94 out of 5 average rating, 18 reviews
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Home in Jaffrey
John's Mountain Hideaway
3 bedrooms, 2 bathrooms
10–15 Sept
5.0 out of 5 average rating, 6 reviews
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Home in West Brattleboro
Private Brookside Farmhouse
3 bedrooms, 4 beds, 1.5 bathrooms
2–7 Sept
4.93 out of 5 average rating, 88 reviews
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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, 12 reviews
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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, 248 reviews
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Home in Rindge
The Shoreline
5 bedrooms, 13 beds, 2.5 bathrooms
8–13 Sept
4.96 out of 5 average rating, 49 reviews
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Campsite in Winchester
Escape to our serene RV pad in Winchester, NH
1 bedroom, 1 bed, 1 bathroom
1–6 Sept
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Flat in Keene
The Murdock Suite @ The Large House
2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
4.95 out of 5 average rating, 80 reviews
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Cabin in West Brattleboro
Hidden Forest Cabin: Kitchen, Deck, Babbling Brook
3 bedrooms, 6 beds, 1 bathroom
2–7 Sept
4.98 out of 5 average rating, 45 reviews
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Flat in Brattleboro
Apt in town 2 BR/2 levels in Victorian Farmhouse
2 bedrooms, 2 queen beds, 1 bathroom
1–6 Sept
4.95 out of 5 average rating, 350 reviews
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Home in Sunderland
Farmhouse on working dairy farm
4 bedrooms, 6 beds, 1.5 bathrooms
6–11 Sept
4.98 out of 5 average rating, 63 reviews
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Home in Royalston
Historic Home w/ Modern Updates on < 4 Acres
4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
4.93 out of 5 average rating, 76 reviews