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Search results; Over 1,000 homes in Winchester

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Guest favourite
Home in Winchester
Highland Lakefront Retreat
4 bedrooms, 5 beds, 2 private bathrooms
4–9 Oct
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4.89 out of 5 average rating, 46 reviews
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Top guest favourite
Home in Winsted
Luxury Highland Lake Waterfront
7 bedrooms, 11 beds, 4 bathrooms
8–13 Sept
5.0 out of 5 average rating, 38 reviews
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Guest favourite
Flat in Winsted
2nd Floor The Inn at Highland Lake
3 bedrooms, 5 beds, 1 bathroom
7–12 Sept
4.91 out of 5 average rating, 67 reviews
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Guest favourite
Home in Winsted
Serene Getaway in the Berkshires
4 bedrooms, 4 beds, 4 bathrooms
1–6 Sept
5.0 out of 5 average rating, 6 reviews
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Top guest favourite
Guest suite in Winchester
Private Suite 2 Bedroom Deck Lake Views
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
4.97 out of 5 average rating, 232 reviews
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Guest favourite
Flat in Winsted
Getaway for a weekend! Close to Ski Sundown.
1 bedroom, 1 bed, 1 bathroom
7–12 Sept
4.92 out of 5 average rating, 145 reviews
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Superhost
Serviced apartment in Winsted
Haven at Highland lake
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
4.87 out of 5 average rating, 183 reviews
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Guest favourite
Guest suite in Torrington
Luxury Loft / Hotel quality Stay
1 bedroom, 1 queen bed, 1 bathroom
30 Oct – 4 Nov
4.96 out of 5 average rating, 55 reviews
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Top guest favourite
Home in Winsted
Newly renovated lakefront home!
4 bedrooms, 7 beds, 2 bathrooms
4–9 Sept
4.95 out of 5 average rating, 39 reviews
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Home in Winsted
Lakefront Escape on Highland
5 bedrooms, 7 beds, 4 bathrooms
1–6 Sept
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Flat in Torrington
“The Clemons!” Central AC - 3 Beds - Main Level
3 bedrooms, 3 beds, 1.5 bathrooms
7–12 Sept
4.99 out of 5 average rating, 158 reviews
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Top guest favourite
Home in Barkhamsted
2BR Family friendly home in Riverton paradise
2 bedrooms, 2 beds, 2 bathrooms
12–17 Sept
4.94 out of 5 average rating, 50 reviews
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Guest favourite
Cottage in New Hartford
Cozy West Hill Lake Cottage Retreat
1 bedroom, 2 double beds, 1 bathroom
8–13 Sept
4.83 out of 5 average rating, 18 reviews
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Home in Winchester
Waterfront & Guest House Available in Winsted, CT!
5 bedrooms, 7 beds, 3 bathrooms
14–19 Sept
New place to stay
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Top guest favourite
Cabin in Harwinton
Beautiful Brook-side Log Cabin on 3 Private Acres
2 bedrooms, 2 queen beds, 1.5 bathrooms
14–19 Sept
4.97 out of 5 average rating, 112 reviews
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Guest favourite
Guest suite in Torrington
Garden Retreat in New England Near Lake & Trails
1 bedroom, 1 bathroom
4–9 Oct
4.81 out of 5 average rating, 133 reviews
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Home in Harwinton
Lake Harwinton Cottage w/ Kayaks & Canoe
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
New place to stay
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Guest favourite
Home in Torrington
Beautiful poolside oasis with large cozy home!
2 bedrooms, 4 beds, 2 bathrooms
1–6 Nov
4.9 out of 5 average rating, 10 reviews
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Top guest favourite
Farm stay in Litchfield
Gray Rock Farm - The whole place to yourself
6 bedrooms, 9 beds, 4 bathrooms
20–25 Oct
4.97 out of 5 average rating, 60 reviews