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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, 1 bathroom
7–12 Sept
4.91 out of 5 average rating, 66 reviews
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
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, 180 reviews
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
Home in Winsted
Lakefront Escape on Highland
5 bedrooms, 7 beds, 4 bathrooms
1–6 Sept
Top guest favourite
Guest suite in Winchester
Private Suite 2 Bedroom Deck Lake Views
2 bedrooms, 2 beds, 1 bathroom
1–6 Sept
4.97 out of 5 average rating, 229 reviews
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
Guest favourite
Room in Barkhamsted
Sweet Suite in Lakefront Chalet-pvt bath
2 beds, 1 bathroom
1–6 Sept
4.88 out of 5 average rating, 159 reviews
Guest favourite
Flat in Winchester
Gateway to the Berkshires
1 bedroom, 5 beds, 1 bathroom
2–7 Oct
4.91 out of 5 average rating, 422 reviews
Top guest favourite
Home in Winsted
Newly renovated lakefront home!
4 bedrooms, 7 beds, 2 bathrooms
1–6 Sept
4.95 out of 5 average rating, 39 reviews
Guest favourite
Cabin in New Hartford
West Hill Cabin
3 bedrooms, 4 beds, 2 bathrooms
11–16 Sept
4.97 out of 5 average rating, 75 reviews
Guest favourite
Home in Winsted
Spacious & serene house in Berkshires
4 bedrooms, 5 beds, 3.5 bathrooms
1–6 Sept
4.92 out of 5 average rating, 25 reviews
Superhost
Cabin in New Hartford
West Hill Cottage-stroll to pristine beach
3 bedrooms, 4 beds, 1.5 bathrooms
1–6 Sept
New place to stay
Top guest favourite
Home in Torrington
The Shirley. A Mid Century Ranch - Central A/C
3 bedrooms, 3 beds, 1 bathroom
1–6 Sept
4.97 out of 5 average rating, 36 reviews
Top guest favourite
Home in Winchester
Highland Lakefront Retreat
4 bedrooms, 5 beds, 2 bathrooms
4–9 Oct
4.93 out of 5 average rating, 44 reviews
Superhost
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
Guest favourite
Guest suite in Torrington
Luxury Loft / Hotel quality Stay
1 bedroom, 1 queen bed, 1 bathroom
25–30 Oct
4.96 out of 5 average rating, 53 reviews
Superhost
Flat in New Hartford
Quiet Wooded Property Near Lake
2 bedrooms, 2 beds, 1 bathroom
10–15 Sept