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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
Superhost
Serviced apartment in Winsted
Haven at Highland lake
1 bedroom, 2 beds
23–28 Aug
4.87 out of 5 average rating, 178 reviews
Guest favourite
Flat in Winsted
2nd Floor The Inn at Highland Lake
3 bedrooms, 5 beds
24–29 Aug
4.91 out of 5 average rating, 65 reviews
Top guest favourite
Home in Winchester
Highland Lakefront Retreat
4 bedrooms, 5 beds
27 Sept – 2 Oct
4.93 out of 5 average rating, 42 reviews
Guest favourite
Flat in Winsted
Getaway for a weekend! Close to Ski Sundown.
1 bedroom, 1 bed
7–12 Sept
4.92 out of 5 average rating, 144 reviews
Top guest favourite
Guest suite in Winchester
Private Suite 2 Bedroom Deck Lake Views
2 bedrooms, 2 beds
23–28 Aug
4.97 out of 5 average rating, 227 reviews
Guest favourite
Home in Winsted
Spacious & serene house in Berkshires
4 bedrooms, 5 beds
25–30 Aug
4.92 out of 5 average rating, 25 reviews
Top guest favourite
Home in Winsted
Newly renovated lakefront home!
4 bedrooms, 7 beds
31 Aug – 5 Sept
4.95 out of 5 average rating, 39 reviews
Superhost
Cabin in New Hartford
West Hill Cottage-stroll to pristine beach
3 bedrooms, 4 beds
23–28 Aug
New place to stay
Top guest favourite
Cottage in Winsted
Cottage Ease.
2 bedrooms, 2 beds
29 Aug – 3 Sept
4.93 out of 5 average rating, 58 reviews
Superhost
Barn in Canaan
The Cobble Barn | Fireplace • A/C • Screened Porch
2 bedrooms, 3 beds
6–11 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
14–19 Sept
4.97 out of 5 average rating, 110 reviews
Superhost
Cottage in New Hartford
Cozy West Hill Lake Cottage Retreat
1 bedroom, 2 double beds
24–29 Aug
4.82 out of 5 average rating, 17 reviews
Top guest favourite
Home in Torrington
The Shirley. A Mid Century Ranch - Central A/C
3 bedrooms, 3 beds
31 Aug – 5 Sept
4.97 out of 5 average rating, 36 reviews
Guest favourite
Home in Winsted
Serene Getaway in the Berkshires
4 bedrooms, 4 beds
21–26 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Guest house in Barkhamsted
Farmington River Carriage House Pleasant Valley CT
2 bedrooms, 3 beds
14–19 Sept
4.91 out of 5 average rating, 121 reviews
Guest favourite
Villa in Winsted
Waterfront Litchfield Hills 1-bdrm Old Mill villa
1 bedroom, 1 bed
22–27 Aug
5.0 out of 5 average rating, 6 reviews
Superhost
Home in Winsted
Renovated lake house, just steps to the water.
3 bedrooms, 4 beds
13–18 Oct
4.81 out of 5 average rating, 62 reviews
Superhost
Flat in New Hartford
Quiet Wooded Property Near Lake
2 bedrooms, 2 beds
10–15 Sept