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

Guest favourite
Flat in Winsted
Inn at Highland Lake: 1st Fl Suite w/ Dock
1 bedroom, 2 beds, 1 private bathroom
22–27 Aug
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4.89 out of 5 average rating, 47 reviews
Superhost
Serviced apartment in Winsted
Haven at Highland lake
1 bedroom, 2 beds, 1 bathroom
23–28 Aug
4.87 out of 5 average rating, 177 reviews
Guest favourite
Flat in Winsted
2nd Floor The Inn at Highland Lake
3 bedrooms, 5 beds, 1 bathroom
24–29 Aug
4.91 out of 5 average rating, 65 reviews
Guest favourite
Flat in Winsted
Getaway for a weekend! Close to Ski Sundown.
1 bedroom, 1 bed, 1 bathroom
16–21 Aug
4.92 out of 5 average rating, 142 reviews
Top guest favourite
Home in Winchester
Highland Lakefront Retreat
4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
4.93 out of 5 average rating, 41 reviews
Guest favourite
Cottage in Winsted
Waterfront Cottage at Highland Lake w/dock
2 bedrooms, 4 beds, 2.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Guest suite in Winchester
Private Suite 2 Bedroom Deck Lake Views
2 bedrooms, 2 beds, 1 bathroom
16–21 Aug
4.97 out of 5 average rating, 226 reviews
Guest favourite
Home in Winsted
Spacious & serene house in Berkshires
4 bedrooms, 5 beds, 3.5 bathrooms
16–21 Aug
4.92 out of 5 average rating, 24 reviews
Guest favourite
Cottage in Winsted
Cottage Ease.
2 bedrooms, 2 beds, 1 bathroom
29 Aug – 3 Sept
4.93 out of 5 average rating, 57 reviews
Top guest favourite
Home in Winsted
Newly renovated lakefront home!
4 bedrooms, 7 beds, 2 bathrooms
31 Aug – 5 Sept
4.95 out of 5 average rating, 39 reviews
Top guest favourite
Home in Torrington
The Shirley. A Mid Century Ranch - Central A/C
3 bedrooms, 3 beds, 1 bathroom
14–19 Aug
4.97 out of 5 average rating, 35 reviews
Superhost
Home in Winsted
Renovated lake house, just steps to the water.
3 bedrooms, 4 beds, 2 bathrooms
17–22 Aug
4.82 out of 5 average rating, 60 reviews
Guest favourite
Tiny home in New Hartford
West Hill Outpost
1 queen bed, 1 bathroom
18–23 Aug
4.9 out of 5 average rating, 98 reviews
Guest favourite
Flat in Winchester
Gateway to the Berkshires
1 bedroom, 5 beds, 1 bathroom
7–12 Sept
4.91 out of 5 average rating, 422 reviews
Top guest favourite
Home in Torrington
Clean & Quiet Home| Enclosed 3 Season Porch & Deck
3 bedrooms, 3 beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 66 reviews
Guest favourite
Home in Winsted
Serene Getaway in the Berkshires
4 bedrooms, 4 beds, 4 bathrooms
12–17 Aug
5.0 out of 5 average rating, 6 reviews
Home in Winchester
Waterfront & Guest House Available in Winsted, CT!
5 bedrooms, 7 beds, 3 bathrooms
13–18 Aug
New place to stay
Home in Winchester
Spacious Lakefront Retreat w/Dock | Close to Town
5 bedrooms, 8 beds, 3 bathrooms
28 Aug – 2 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Cabin in Harwinton
Beautiful Brook-side Log Cabin on 3 Private Acres
2 bedrooms, 2 queen beds, 1.5 bathrooms
16–21 Aug
4.97 out of 5 average rating, 109 reviews