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

Guest favourite
Cottage in Winsted
Cottage Ease.
2 bedrooms, 2 beds, 1 private bathroom
1–6 Nov
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4.93 out of 5 average rating, 59 reviews
Guest favourite
Flat in Winsted
Getaway for a weekend! Close to Ski Sundown.
1 bedroom, 1 bed, 1 bathroom
14–19 Sept
4.91 out of 5 average rating, 148 reviews
Guest favourite
Flat in Winsted
2nd Floor The Inn at Highland Lake
3 bedrooms, 5 beds, 1 bathroom
14–19 Sept
4.91 out of 5 average rating, 67 reviews
Top guest favourite
Home in Winsted
Luxury Highland Lake Waterfront
7 bedrooms, 11 beds, 4 bathrooms
15–20 Sept
5.0 out of 5 average rating, 38 reviews
Superhost
Serviced apartment in Winsted
Haven at Highland lake
1 bedroom, 2 beds, 1 bathroom
27 Sept – 2 Oct
4.87 out of 5 average rating, 185 reviews
Guest favourite
Flat in Winchester
Gateway to the Berkshires
1 bedroom, 5 beds, 1 bathroom
24–29 Sept
4.91 out of 5 average rating, 422 reviews
Top guest favourite
Guest suite in Winchester
Private Suite 2 Bedroom Deck Lake Views
2 bedrooms, 2 beds, 1 bathroom
27 Sept – 2 Oct
4.97 out of 5 average rating, 235 reviews
Guest favourite
Home in Winsted
Serene Getaway in the Berkshires
4 bedrooms, 4 beds, 4 bathrooms
14–19 Sept
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Winchester
Highland Lakefront Retreat
4 bedrooms, 5 beds, 2 bathrooms
4–9 Oct
4.9 out of 5 average rating, 48 reviews
Guest favourite
Home in Winsted
Winsted /Winchester House wifi high speed internet
4 bedrooms, 6 beds, 2 bathrooms
16–22 Sept
4.89 out of 5 average rating, 36 reviews
Guest favourite
Room in Barkhamsted
Sweet Suite in Lakefront Chalet-pvt bath
2 beds, 1 bathroom
15–20 Sept
4.88 out of 5 average rating, 159 reviews
Top guest favourite
Flat in Torrington
“The Clemons!” Central AC - 3 Beds - Main Level
3 bedrooms, 3 beds, 1.5 bathrooms
26–31 Oct
4.99 out of 5 average rating, 159 reviews
Guest favourite
Flat in Torrington
Modern/Private Five ★ /Hotel quality stay/1 BR Apt
1 bedroom, 1 queen bed, 1 bathroom
3–8 Dec
4.95 out of 5 average rating, 292 reviews
Top guest favourite
Cabin in New Hartford
West Hill Cabin
3 bedrooms, 4 beds, 2 bathrooms
7–12 Oct
4.97 out of 5 average rating, 77 reviews
Top guest favourite
Home in Torrington
Clean & Quiet Home| Enclosed 3 Season Porch & Deck
3 bedrooms, 3 beds, 1 bathroom
26 Sept – 1 Oct
5.0 out of 5 average rating, 69 reviews
Superhost
Flat in New Hartford
Quiet Wooded Property Near Lake
2 bedrooms, 2 beds, 1 bathroom
6–11 Nov
Top guest favourite
Home in Winsted
Newly renovated lakefront home!
4 bedrooms, 7 beds, 2 bathrooms
20–25 Sept
4.95 out of 5 average rating, 39 reviews
Home in Winsted
Lakefront Escape on Highland
5 bedrooms, 7 beds, 4 bathrooms
21–26 Sept
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Winsted
Renovated lake house, just steps to the water.
3 bedrooms, 4 beds, 2 bathrooms
13–18 Oct
4.8 out of 5 average rating, 65 reviews