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

Superhost
Serviced apartment in Winsted
Haven at Highland lake
1 bedroom, 2 beds, 1 private bathroom
23–28 Aug
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4.87 out of 5 average rating, 175 reviews
Guest favourite
Flat in Winsted
Getaway for a weekend! Close to Ski Sundown.
1 bedroom, 1 bed
16–21 Aug
4.92 out of 5 average rating, 142 reviews
Top guest favourite
Guest suite in Winchester
Private Suite 2 Bedroom Deck Lake Views
2 bedrooms, 2 beds
9–14 Aug
4.97 out of 5 average rating, 225 reviews
Home in Winchester
Waterfront & Guest House Available in Winsted, CT!
5 bedrooms, 7 beds
12–17 Aug
New place to stay
Top guest favourite
Room in Norfolk
Norfolk's Charming Suite in the heart of town
1 queen bed
9–14 Aug
4.94 out of 5 average rating, 145 reviews
Guest favourite
Room in Barkhamsted
Sweet Suite in Lakefront Chalet-pvt bath
2 beds
17–22 Aug
4.88 out of 5 average rating, 159 reviews
Superhost
Cabin in New Hartford
West Hill Cottage-stroll to pristine beach
3 bedrooms, 4 beds
10–15 Aug
New place to stay
Top guest favourite
Home in Winchester
Highland Lakefront Retreat
4 bedrooms, 5 beds
20–25 Sept
4.95 out of 5 average rating, 39 reviews
Guest favourite
Flat in Torrington
Modern/Private Five ★ /Hotel quality stay/1 BR Apt
1 bedroom, 1 queen bed
23–28 Aug
4.95 out of 5 average rating, 284 reviews
Superhost
Home in New Hartford
Sunset Pad. Lakefront for 2, private dock & SUPs.
1 bedroom, 1 king bed
30 Aug – 4 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Flat in Winsted
Inn at Highland Lake: 1st Fl Suite w/ Dock
1 bedroom, 2 beds
4–9 Aug
4.89 out of 5 average rating, 47 reviews
Top guest favourite
Home in Torrington
Enjoy the NW Hills, then relax by the river…
3 bedrooms, 4 beds
10–15 Aug
5.0 out of 5 average rating, 11 reviews
Guest favourite
Cottage in Winsted
Waterfront Cottage at Highland Lake w/dock
2 bedrooms, 4 beds
31 Aug – 5 Sept
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Home in Barkhamsted
3BR Family friendly home in Riverton paradise
3 bedrooms, 5 beds
12–17 Sept
4.95 out of 5 average rating, 37 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
Flat in Torrington
Charming Private Apartment Near Downtown
2 bedrooms, 2 queen beds
9–14 Aug
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Winsted
Winsted /Winchester House wifi high speed internet
4 bedrooms, 6 beds
10–16 Aug
4.89 out of 5 average rating, 36 reviews
Guest favourite
Tiny home in New Hartford
West Hill Outpost
1 queen bed
14–19 Aug
4.9 out of 5 average rating, 98 reviews
Guest favourite
Flat in Winchester
Gateway to the Berkshires
1 bedroom, 5 beds
7–12 Sept
4.91 out of 5 average rating, 422 reviews