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

Guest favourite
Cottage in Winsted
Waterfront Cottage at Highland Lake w/dock
2 bedrooms, 4 beds, 2.5 private bathrooms
1–6 May
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5.0 out of 5 average rating, 17 reviews
Guest favourite
Flat in Winsted
2nd Floor The Inn at Highland Lake
3 bedrooms, 5 beds
7–12 Sept
4.91 out of 5 average rating, 67 reviews
Top guest favourite
Home in Winsted
Luxury Highland Lake Waterfront
7 bedrooms, 11 beds
8–13 Sept
5.0 out of 5 average rating, 38 reviews
Superhost
Serviced apartment in Winsted
Haven at Highland lake
1 bedroom, 2 beds
20–25 Sept
4.87 out of 5 average rating, 184 reviews
Guest favourite
Flat in Winsted
Getaway for a weekend! Close to Ski Sundown.
1 bedroom, 1 bed
7–12 Sept
4.92 out of 5 average rating, 145 reviews
Home in Winchester
Winsted Lakefront Escape: Dock & Fire Pit
3 bedrooms, 7 beds
3–10 Sept
New place to stay
Top guest favourite
Home in Barkhamsted
2BR Family friendly home in Riverton paradise
2 bedrooms, 2 beds
12–17 Sept
4.9 out of 5 average rating, 51 reviews
Guest favourite
Home in Winsted
Serene Getaway in the Berkshires
4 bedrooms, 4 beds
2–7 Sept
5.0 out of 5 average rating, 6 reviews
Superhost
Flat in New Hartford
Quiet Wooded Property Near Lake
2 bedrooms, 2 beds
10–15 Sept
Top guest favourite
Home in Winsted
Newly renovated lakefront home!
4 bedrooms, 7 beds
4–9 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
19–24 Sept
4.97 out of 5 average rating, 232 reviews
Guest favourite
Cabin in New Hartford
West Hill Cabin
3 bedrooms, 4 beds
11–16 Sept
4.97 out of 5 average rating, 75 reviews
Top guest favourite
Flat in Torrington
“The Clemons!” Central AC - 3 Beds - Main Level
3 bedrooms, 3 beds
7–12 Sept
4.99 out of 5 average rating, 158 reviews
Guest favourite
Cottage in New Hartford
West Hill Lake Cottage with Private Beach Access
1 bedroom, 2 double beds
8–13 Sept
4.83 out of 5 average rating, 18 reviews
Home in Winsted
Lakefront Escape on Highland
5 bedrooms, 7 beds
2–7 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Torrington
Pristine Downtown 2BR Cozy Fireplace & Parking
2 bedrooms, 2 queen beds
20–25 Sept
5.0 out of 5 average rating, 123 reviews
Guest favourite
Home in Winchester
Highland Lakefront Retreat
4 bedrooms, 5 beds
4–9 Oct
4.89 out of 5 average rating, 46 reviews
Guest favourite
Tiny home in New Hartford
West Hill Outpost
1 queen bed
10–15 Sept
4.9 out of 5 average rating, 99 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