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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, 168 reviews
Guest favourite
Flat in Winsted
2nd Floor The Inn at Highland Lake
3 bedrooms, 5 beds, 1 bathroom
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, 3 bathrooms
7–12 Jul
Top guest favourite
Home in Winchester
Highland Lakefront Retreat
4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
4.94 out of 5 average rating, 32 reviews
Superhost
Home in Winsted
Renovated lake house, just steps to the water.
3 bedrooms, 4 beds, 2 bathrooms
26–31 Jul
4.81 out of 5 average rating, 59 reviews
Top guest favourite
Home in Winsted
Newly renovated lakefront home!
4 bedrooms, 7 beds, 2 bathrooms
18–23 Jul
4.95 out of 5 average rating, 38 reviews
Guest favourite
Cottage in Winsted
Cottage Ease.
2 bedrooms, 2 beds, 1 bathroom
26–31 Jul
4.93 out of 5 average rating, 54 reviews
Guest favourite
Cottage in Winsted
Waterfront Cottage at Highland Lake w/dock
2 bedrooms, 4 beds, 2.5 bathrooms
31 Aug – 5 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
11–16 Jul
4.97 out of 5 average rating, 212 reviews
Guest favourite
Flat in Winsted
Getaway for a weekend! Close to Ski Sundown.
1 bedroom, 1 bed, 1 bathroom
1–6 Aug
4.91 out of 5 average rating, 140 reviews
Guest favourite
Home in Winsted
Spacious & serene house in Berkshires
4 bedrooms, 5 beds, 3.5 bathrooms
28 Jul – 2 Aug
4.89 out of 5 average rating, 19 reviews
Place to stay in New Hartford
Private Room in Mid-Century Modern Artist House
1 bedroom, 1 bed, 1 bathroom
6–11 Jul
New place to stay
Top guest favourite
Flat in Torrington
“The Clemons!” Central AC - 3 Beds - Main Level
3 bedrooms, 3 beds, 1.5 bathrooms
16–21 Aug
4.99 out of 5 average rating, 151 reviews
Guest favourite
Home in Winsted
Lake House- Great for Families
5 bedrooms, 7 beds, 3.5 bathrooms
12–18 Aug
4.98 out of 5 average rating, 64 reviews
Top guest favourite
Home in Litchfield County
70's Retro House
2 bedrooms, 2 queen beds, 2 bathrooms
1–6 Jul
4.96 out of 5 average rating, 24 reviews
Flat in Torrington
Charming Private Apartment Near Downtown
2 bedrooms, 2 queen beds, 1 bathroom
1–6 Jul
New place to stay
Home in Torrington
Litchfield Retreat, Wineries, Foliage & Skiing
2 bedrooms, 3 beds, 1 bathroom
1–6 Jul
4.56 out of 5 average rating, 9 reviews
Home in Thomaston
Tranquil Farmhouse Retreat Full Home
4 bedrooms, 6 beds, 3 bathrooms
18–23 Jul
New place to stay
Guest favourite
Tiny home in New Hartford
West Hill Outpost
1 queen bed, 1 bathroom
7–12 Jul
4.89 out of 5 average rating, 94 reviews