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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
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
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
Home in Barkhamsted
2BR Family friendly home in Riverton paradise
2 bedrooms, 2 beds, 2 bathrooms
7–12 Aug
4.94 out of 5 average rating, 49 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
Villa in Winsted
Waterfront Litchfield Hills 1-bdrm Old Mill villa
1 bedroom, 1 bed, 1.5 bathrooms
1–6 Jul
5.0 out of 5 average rating, 5 reviews
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
Superhost
Home in New Hartford
Sunset Pad. Lakefront for 2, private dock & SUPs.
1 bedroom, 1 king bed, 1 bathroom
13–18 Jul
New place to stay
Guest favourite
Guest suite in Torrington
Luxury Loft / Hotel quality Stay
1 bedroom, 1 queen bed, 1 bathroom
12–17 Jul
4.98 out of 5 average rating, 42 reviews
Guest suite in Torrington
Garden Retreat in New England Near Lake & Trails
1 bedroom, 1 bathroom
12–17 Aug
4.8 out of 5 average rating, 119 reviews
Guest favourite
Cabin in New Hartford
West Hill Cabin
3 bedrooms, 4 beds, 2 bathrooms
22–27 Jul
4.97 out of 5 average rating, 71 reviews
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
Guest favourite
Flat in Winchester
Gateway to the Berkshires
1 bedroom, 5 beds, 1 bathroom
31 Aug – 5 Sept
4.9 out of 5 average rating, 421 reviews
Top guest favourite
Home in Torrington
Clean & Quiet Home| Enclosed 3 Season Porch & Deck
3 bedrooms, 3 beds, 1 bathroom
5–10 Jul
5.0 out of 5 average rating, 57 reviews
Home in Torrington
Enjoy the NW Hills, then relax by the river…
3 bedrooms, 4 beds, 2 bathrooms
26–31 Jul
New place to stay
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 New Hartford
Cozy West Hill Lake Cottage Retreat
1 bedroom, 2 double beds, 1 bathroom
14–19 Jul
4.92 out of 5 average rating, 13 reviews
Top guest favourite
Home in Colebrook
Norbrook Farm ~ Rustic farmhouse w/ pond & trails
3 bedrooms, 4 beds, 2 bathrooms
21–26 Jul
4.99 out of 5 average rating, 243 reviews