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

Guest favourite
Serviced apartment in Winsted
Haven at Highland lake
1 bedroom, 2 beds, 1 private bathroom
5–10 Jul
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4.89 out of 5 average rating, 167 reviews
Top guest favourite
Home in Winchester
Highland Lakefront Retreat
4 bedrooms, 5 beds
20–25 Sept
4.94 out of 5 average rating, 32 reviews
Guest favourite
Flat in Winsted
2nd Floor The Inn at Highland Lake
3 bedrooms, 5 beds
5–10 Jul
4.91 out of 5 average rating, 65 reviews
Home in Winchester
Spacious Lakefront Retreat w/Dock | Close to Town
5 bedrooms, 8 beds
7–12 Jul
Guest favourite
Cottage in Winsted
Cottage Ease.
2 bedrooms, 2 beds
26–31 Jul
4.93 out of 5 average rating, 54 reviews
Superhost
Home in Winsted
Renovated lake house, just steps to the water.
3 bedrooms, 4 beds
26–31 Jul
4.81 out of 5 average rating, 59 reviews
Guest favourite
Flat in Winsted
Getaway for a weekend! Close to Ski Sundown.
1 bedroom, 1 bed
1–6 Aug
4.91 out of 5 average rating, 140 reviews
Top guest favourite
Home in Winsted
Newly renovated lakefront home!
4 bedrooms, 7 beds
18–23 Jul
4.95 out of 5 average rating, 38 reviews
Place to stay in New Hartford
Private Room in Mid-Century Modern Artist House
1 bedroom, 1 bed
6–11 Jul
New place to stay
Top guest favourite
Guest suite in Winchester
Private Suite 2 Bedroom Deck Lake Views
2 bedrooms, 2 beds
11–16 Jul
4.97 out of 5 average rating, 211 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
Guest favourite
Home in Winsted
Spacious & serene house in Berkshires
4 bedrooms, 5 beds
28 Jul – 2 Aug
4.89 out of 5 average rating, 19 reviews
Top guest favourite
Flat in Torrington
“The Clemons!” Central AC - 3 Beds - Main Level
3 bedrooms, 3 beds
16–21 Aug
4.99 out of 5 average rating, 151 reviews
Flat in Torrington
Charming Private Apartment Near Downtown
2 bedrooms, 2 queen beds
1–6 Jul
New place to stay
Top guest favourite
Home in Litchfield County
70's Retro House
2 bedrooms, 2 queen beds
1–6 Jul
4.96 out of 5 average rating, 24 reviews
Guest favourite
Home in Winsted
Lake House- Great for Families
5 bedrooms, 7 beds
12–18 Aug
4.98 out of 5 average rating, 64 reviews
Home in Torrington
Litchfield Retreat, Wineries, Foliage & Skiing
2 bedrooms, 3 beds
1–6 Jul
4.56 out of 5 average rating, 9 reviews
Guest favourite
Flat in Winchester
Gateway to the Berkshires
1 bedroom, 5 beds
31 Aug – 5 Sept
4.9 out of 5 average rating, 421 reviews
Flat in Torrington
3 Bedroom 2 Bath apartment near downtown.
3 bedrooms, 4 beds
14–19 Jul