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Search results; Over 1,000 homes in Winchester

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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, 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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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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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
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
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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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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Home in Guilford
Writers Retreat! Peace and solitude.
1 bedroom, 1 queen bed, 1 bathroom
1–6 Oct
New place to stay
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Home in Westmoreland
Tasteful Country Home on 5 Acres ~ 3 Mi to Lake!
3 bedrooms, 3 beds, 1 bathroom
1–6 Oct
4.93 out of 5 average rating, 14 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, 105 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
Flat in Vernon
Farm land view.
1 bedroom, 1 queen bed, 1 bathroom
13–18 Oct
4.95 out of 5 average rating, 196 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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Top guest favourite
Cabin in West Brattleboro
Hidden Forest Cabin: Kitchen, Deck, Babbling Brook
3 bedrooms, 6 beds, 1 bathroom
14–19 Oct
4.98 out of 5 average rating, 47 reviews
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Home in Royalston
Historic Home w/ Modern Updates on < 4 Acres
4 bedrooms, 5 beds, 2 bathrooms
11–16 Oct
4.94 out of 5 average rating, 77 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, 516 reviews
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Guest favourite
Home in West Brattleboro
Private Brookside Farmhouse
3 bedrooms, 4 beds, 1.5 bathrooms
13–18 Oct
4.93 out of 5 average rating, 88 reviews