filters

Search results; Over 1,000 homes in Winchester

Top guest favourite
Guest suite in Winchester
Private Suite 2 Bedroom Deck Lake Views
2 bedrooms, 2 beds, 1 private bathroom
19–24 Sept
,
4.97 out of 5 average rating, 235 reviews
Guest favourite
Home in Winchester
Highland Lakefront Retreat
5 beds
4–9 Oct
4.9 out of 5 average rating, 48 reviews
Top guest favourite
Home in Winsted
Newly renovated lakefront home!
7 beds
20–25 Sept
4.95 out of 5 average rating, 39 reviews
Guest favourite
Flat in Winchester
Gateway to the Berkshires
5 beds
2–7 Oct
4.91 out of 5 average rating, 422 reviews
Guest favourite
Flat in Winsted
2nd Floor The Inn at Highland Lake
5 beds
12–17 Sept
4.91 out of 5 average rating, 67 reviews
Top guest favourite
Home in Winsted
Luxury Highland Lake Waterfront
11 beds
12–17 Sept
5.0 out of 5 average rating, 38 reviews
Home in Winchester
Waterfront & Guest House Available in Winsted, CT!
7 beds
20–25 Sept
New place to stay
Home in Winsted
Lakefront Escape on Highland
7 beds
21–26 Sept
5.0 out of 5 average rating, 3 reviews
Superhost
Flat in Winsted
Haven at Highland lake
2 beds
27 Sept – 2 Oct
4.87 out of 5 average rating, 184 reviews
Guest favourite
Cottage in Winchester
Winsted/Highland Lake/Direct Waterfront/Immaculate
8 beds
25–30 Oct
4.97 out of 5 average rating, 79 reviews
Guest favourite
Home in Winsted
Winsted /Winchester House wifi high speed internet
6 beds
13–19 Sept
4.89 out of 5 average rating, 36 reviews
Guest favourite
Home in Winchester
Bluebird School House
2 beds
13–18 Sept
5.0 out of 5 average rating, 8 reviews
Home in Winchester
Spacious Lakefront Retreat w/Dock | Close to Town
8 beds
12–17 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Torrington
Clean & Quiet Home| Enclosed 3 Season Porch & Deck
3 beds
12–17 Sept
5.0 out of 5 average rating, 69 reviews
Guest favourite
Home in Winsted
Serene Getaway in the Berkshires
4 beds
12–17 Sept
5.0 out of 5 average rating, 6 reviews
Guest favourite
Flat in Winsted
Getaway for a weekend! Close to Ski Sundown.
1 bed
13–18 Sept
4.9 out of 5 average rating, 147 reviews
Superhost
Home in Winsted
Renovated lake house, just steps to the water.
4 beds
13–18 Oct
4.8 out of 5 average rating, 64 reviews
Home in Harwinton
Lake Harwinton Cottage w/ Kayaks & Canoe
3 beds
13–18 Sept
New place to stay
Top guest favourite
Home in Barkhamsted
3BR Family friendly home in Riverton paradise
5 beds
2–7 Nov
4.95 out of 5 average rating, 38 reviews