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Search results; Over 1,000 homes in Winchester

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Top guest favourite
Guest suite in Winchester
Private Suite 2 Bedroom Deck Lake Views
2 bedrooms, 2 beds, 1 private bathroom
27 Sept – 2 Oct
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4.97 out of 5 average rating, 235 reviews
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Guest favourite
Home in Winchester
Highland Lakefront Retreat
4 bedrooms, 5 beds, 2 bathrooms
4–9 Oct
4.9 out of 5 average rating, 49 reviews
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Guest favourite
Flat in Winchester
Gateway to the Berkshires
1 bedroom, 5 beds, 1 bathroom
24–29 Sept
4.91 out of 5 average rating, 422 reviews
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Superhost
Flat in Winsted
Haven at Highland lake
1 bedroom, 2 beds, 1 bathroom
27 Sept – 2 Oct
4.87 out of 5 average rating, 185 reviews
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Top guest favourite
Home in Winsted
Newly renovated lakefront home!
4 bedrooms, 7 beds, 2 bathrooms
20–25 Sept
4.95 out of 5 average rating, 40 reviews
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Guest favourite
Flat in Winsted
2nd Floor The Inn at Highland Lake
3 bedrooms, 5 beds, 1 bathroom
17–22 Sept
4.91 out of 5 average rating, 67 reviews
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Top guest favourite
Home in Winsted
Luxury Highland Lake Waterfront
7 bedrooms, 11 beds, 4 bathrooms
18–23 Sept
5.0 out of 5 average rating, 38 reviews
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Home in Winsted
Lakefront Escape on Highland
5 bedrooms, 7 beds, 4 bathrooms
21–26 Sept
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Home in New Hartford
Mountaintop Nirvana: Lake, Hot Tub, Pool Table
5 bedrooms, 6 beds, 3 bathrooms
2–7 Oct
4.9 out of 5 average rating, 87 reviews
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Home in Winchester
Waterfront & Guest House Available in Winsted, CT!
5 bedrooms, 7 beds, 3 bathrooms
20–25 Sept
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Home in Winchester
Spacious Lakefront Retreat w/Dock | Close to Town
5 bedrooms, 8 beds, 3 bathrooms
20–25 Sept
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Home in Torrington
Clean & Quiet Home| Enclosed 3 Season Porch & Deck
3 bedrooms, 3 beds, 1 bathroom
26 Sept – 1 Oct
5.0 out of 5 average rating, 69 reviews
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Guest favourite
Cottage in Winchester
Winsted/Highland Lake/Direct Waterfront/Immaculate
3 bedrooms, 8 beds, 2 bathrooms
25–30 Oct
4.97 out of 5 average rating, 79 reviews
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Superhost
Home in Winsted
Renovated lake house, just steps to the water.
3 bedrooms, 4 beds, 2 bathrooms
13–18 Oct
4.8 out of 5 average rating, 65 reviews
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Guest favourite
Flat in Winsted
Getaway for a weekend! Close to Ski Sundown.
1 bedroom, 1 bed, 1 bathroom
17–22 Sept
4.91 out of 5 average rating, 148 reviews
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Superhost
Cabin in New Hartford
West Hill Cottage-stroll to pristine beach
3 bedrooms, 4 beds, 1.5 bathrooms
18–23 Sept
New place to stay
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Guest favourite
Home in Winsted
Serene Getaway in the Berkshires
4 bedrooms, 4 beds, 4 bathrooms
17–22 Sept
5.0 out of 5 average rating, 6 reviews
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Guest favourite
Home in Winsted
Spacious & serene house in Berkshires
4 bedrooms, 5 beds, 3.5 bathrooms
20–25 Sept
4.92 out of 5 average rating, 25 reviews
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Top guest favourite
Home in Winchester
Bluebird School House
1 bedroom, 2 beds, 1 bathroom
26–31 Oct
5.0 out of 5 average rating, 10 reviews