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Search results; Over 1,000 homes in Winsted, Winchester

Superhost
Flat in Winsted
Haven at Highland lake
1 bedroom, 2 beds, 1 private bathroom
27 Sept – 2 Oct
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4.87 out of 5 average rating, 184 reviews
Guest favourite
Flat in Winsted
2nd Floor The Inn at Highland Lake
3 bedrooms, 5 beds
12–17 Sept
4.91 out of 5 average rating, 67 reviews
Guest favourite
Flat in Winsted
Getaway for a weekend! Close to Ski Sundown.
1 bedroom, 1 bed
13–18 Sept
4.9 out of 5 average rating, 147 reviews
Top guest favourite
Home in Winsted
Luxury Highland Lake Waterfront
7 bedrooms, 11 beds
13–18 Sept
5.0 out of 5 average rating, 38 reviews
Guest favourite
Home in Winchester
Highland Lakefront Retreat
4 bedrooms, 5 beds
4–9 Oct
4.9 out of 5 average rating, 48 reviews
Guest favourite
Flat in Winchester
Gateway to the Berkshires
1 bedroom, 5 beds
2–7 Oct
4.91 out of 5 average rating, 422 reviews
Guest favourite
Home in Winsted
Serene Getaway in the Berkshires
4 bedrooms, 4 beds
12–17 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Winsted
Newly renovated lakefront home!
4 bedrooms, 7 beds
20–25 Sept
4.95 out of 5 average rating, 39 reviews
Top guest favourite
Guest suite in Winchester
Private Suite 2 Bedroom Deck Lake Views
2 bedrooms, 2 beds
27 Sept – 2 Oct
4.97 out of 5 average rating, 235 reviews
Top guest favourite
Cabin in New Hartford
West Hill Cabin
3 bedrooms, 4 beds
7–12 Oct
4.97 out of 5 average rating, 77 reviews
Top guest favourite
Flat in Torrington
“The Clemons!” Central AC - 3 Beds - Main Level
3 bedrooms, 3 beds
26–31 Oct
4.99 out of 5 average rating, 159 reviews
Superhost
Flat in New Hartford
Quiet Wooded Property Near Lake
2 bedrooms, 2 beds
6–11 Nov
Guest favourite
Tiny home in New Hartford
West Hill Outpost
1 queen bed
22–27 Sept
4.89 out of 5 average rating, 101 reviews
Guest favourite
Home in Winsted
Winsted /Winchester House wifi high speed internet
4 bedrooms, 6 beds
14–20 Sept
4.89 out of 5 average rating, 36 reviews
Guest favourite
Room in Barkhamsted
Sweet Suite in Lakefront Chalet-pvt bath
2 beds
13–18 Sept
4.88 out of 5 average rating, 159 reviews
Top guest favourite
Home in Colebrook
Stunning Views of the Berkshire Foothills
3 bedrooms, 4 beds
17–22 Sept
5.0 out of 5 average rating, 33 reviews
Guest favourite
Cottage in Barkhamsted
Cottage - 2 bdr - West Hill Lake w/ Private Beach
2 bedrooms, 3 beds
16–21 May
4.97 out of 5 average rating, 30 reviews
Top guest favourite
Home in Harwinton
1800’s Farmhouse in the hills of Litchfield County
4 bedrooms, 5 beds
13–18 Sept
5.0 out of 5 average rating, 32 reviews
Top guest favourite
Home in Torrington
The Shirley, Quiet Mid Century Ranch -Central A/C
3 bedrooms, 3 beds
25–30 Oct
4.97 out of 5 average rating, 38 reviews