filters

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

Photo 1 of 11
Superhost
Flat in Winsted
Haven at Highland lake
1 bedroom, 2 beds, 1 private bathroom
27 Sept – 2 Oct
,
4.87 out of 5 average rating, 185 reviews
Photo 1 of 29
Guest favourite
Flat in Winsted
2nd Floor The Inn at Highland Lake
3 bedrooms, 5 beds
19–24 Sept
4.91 out of 5 average rating, 67 reviews
Photo 1 of 29
Guest favourite
Flat in Winchester
Gateway to the Berkshires
1 bedroom, 5 beds
5–10 Oct
4.91 out of 5 average rating, 422 reviews
Photo 1 of 23
Guest favourite
Flat in Winsted
Getaway for a weekend! Close to Ski Sundown.
1 bedroom, 1 bed
20–25 Sept
4.91 out of 5 average rating, 148 reviews
Photo 1 of 29
Guest favourite
Home in Winchester
Highland Lakefront Retreat
4 bedrooms, 5 beds
4–9 Oct
4.9 out of 5 average rating, 49 reviews
Photo 1 of 29
Top guest favourite
Home in Winsted
Newly renovated lakefront home!
4 bedrooms, 7 beds
27 Sept – 2 Oct
4.95 out of 5 average rating, 40 reviews
Photo 1 of 29
Guest favourite
Home in Winsted
Spacious & serene house in Berkshires
4 bedrooms, 5 beds
27 Sept – 2 Oct
4.92 out of 5 average rating, 25 reviews
Photo 1 of 20
Superhost
Home in Winsted
Renovated lake house, just steps to the water.
3 bedrooms, 4 beds
13–18 Oct
4.8 out of 5 average rating, 65 reviews
Photo 1 of 29
Top guest favourite
Home in Winsted
Luxury Highland Lake Waterfront
7 bedrooms, 11 beds
20–25 Sept
5.0 out of 5 average rating, 38 reviews
Photo 1 of 29
Home in Winsted
Lakefront Escape on Highland
5 bedrooms, 7 beds
21–26 Sept
5.0 out of 5 average rating, 3 reviews
Photo 1 of 29
Guest favourite
Cottage in Winsted
Waterfront Cottage at Highland Lake w/dock
2 bedrooms, 4 beds
19–24 Sept
5.0 out of 5 average rating, 17 reviews
Photo 1 of 29
Home in Winchester
Spacious Lakefront Retreat w/Dock | Close to Town
5 bedrooms, 8 beds
20–25 Sept
5.0 out of 5 average rating, 4 reviews
Photo 1 of 29
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
Photo 1 of 29
Guest favourite
Home in Winsted
Winsted /Winchester House wifi high speed internet
4 bedrooms, 6 beds
21–27 Sept
4.89 out of 5 average rating, 36 reviews
Photo 1 of 25
Guest favourite
Cottage in Winsted
Cottage Ease.
2 bedrooms, 2 beds
1–6 Nov
4.93 out of 5 average rating, 59 reviews
Photo 1 of 27
Guest favourite
Home in Winsted
Serene Getaway in the Berkshires
4 bedrooms, 4 beds
19–24 Sept
5.0 out of 5 average rating, 6 reviews
Photo 1 of 29
Guest favourite
Cottage in Winchester
Winsted/Highland Lake/Direct Waterfront/Immaculate
3 bedrooms, 8 beds
25–30 Oct
4.97 out of 5 average rating, 79 reviews
Photo 1 of 29
Top guest favourite
Flat in Torrington
Pristine 2BR | Fall Getaway | Fireplace + Parking
2 bedrooms, 2 queen beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 125 reviews
Photo 1 of 29
Top guest favourite
Home in New Hartford
Mountaintop Nirvana: Lake, Hot Tub, Pool Table
5 bedrooms, 6 beds
2–7 Oct
4.9 out of 5 average rating, 87 reviews