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

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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
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Superhost
Serviced apartment in Winsted
Haven at Highland lake
1 bedroom, 2 beds
20–25 Sept
4.87 out of 5 average rating, 182 reviews
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Guest favourite
Flat in Winsted
2nd Floor The Inn at Highland Lake
3 bedrooms, 5 beds
7–12 Sept
4.91 out of 5 average rating, 66 reviews
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Home in Winchester
Highland Lakefront Retreat
4 bedrooms, 5 beds
4–9 Oct
4.93 out of 5 average rating, 44 reviews
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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, 145 reviews
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Top guest favourite
Home in Winsted
Luxury Highland Lake Waterfront
7 bedrooms, 11 beds
8–13 Sept
5.0 out of 5 average rating, 38 reviews
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Top guest favourite
Home in Winsted
Newly renovated lakefront home!
4 bedrooms, 7 beds
1–6 Sept
4.95 out of 5 average rating, 39 reviews
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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
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Guest favourite
Home in Winsted
Spacious & serene house in Berkshires
4 bedrooms, 5 beds
15–20 Sept
4.92 out of 5 average rating, 25 reviews
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Top guest favourite
Home in Colebrook
Riverton Retreat | Entire Home Farmington River
3 bedrooms, 4 beds
1–6 Sept
5.0 out of 5 average rating, 7 reviews
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Home in Winchester
Spacious Lakefront Retreat w/Dock | Close to Town
5 bedrooms, 8 beds
8–13 Sept
5.0 out of 5 average rating, 4 reviews
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Guest favourite
Home in Winsted
Serene Getaway in the Berkshires
4 bedrooms, 4 beds
1–6 Sept
5.0 out of 5 average rating, 6 reviews
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Home in Winsted
Lakefront Escape on Highland
5 bedrooms, 7 beds
1–6 Sept
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Cottage in Winsted
Cottage Ease.
2 bedrooms, 2 beds
16–21 Oct
4.93 out of 5 average rating, 58 reviews
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Guest suite in Winchester
Private Suite 2 Bedroom Deck Lake Views
2 bedrooms, 2 beds
9–14 Sept
4.97 out of 5 average rating, 231 reviews
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Top guest favourite
Home in Torrington
The Shirley. A Mid Century Ranch - Central A/C
3 bedrooms, 3 beds
1–6 Sept
4.97 out of 5 average rating, 36 reviews
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Home in New Hartford
Mountaintop Nirvana: Lake, Hot Tub, Pool Table
5 bedrooms, 6 beds
13–18 Sept
4.89 out of 5 average rating, 84 reviews
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Home in New Hartford
Modern Farmhouse
3 bedrooms, 3 queen beds
8–13 Sept
4.89 out of 5 average rating, 158 reviews
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Flat in Torrington
“The Clemons!” Central AC - 3 Beds - Main Level
3 bedrooms, 3 beds
7–12 Sept
4.99 out of 5 average rating, 158 reviews