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Search results; Over 1,000 homes in Winchester

Top guest favourite
Guest suite in Winchester
Private Suite 2 Bedroom Deck Lake Views
2 bedrooms, 2 beds, 1 private bathroom
19–24 Sept
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4.97 out of 5 average rating, 235 reviews
Guest favourite
Home in Winchester
Highland Lakefront Retreat
4 bedrooms, 5 beds, 2 bathrooms
4–9 Oct
4.89 out of 5 average rating, 47 reviews
Top guest favourite
Home in Winsted
Luxury Highland Lake Waterfront
7 bedrooms, 11 beds, 4 bathrooms
11–16 Sept
5.0 out of 5 average rating, 38 reviews
Home in Winchester
Waterfront & Guest House Available in Winsted, CT!
5 bedrooms, 7 beds, 3 bathrooms
20–25 Sept
New place to stay
Guest favourite
Flat in Winsted
2nd Floor The Inn at Highland Lake
3 bedrooms, 5 beds, 1 bathroom
10–15 Sept
4.91 out of 5 average rating, 67 reviews
Top guest favourite
Home in Winsted
Newly renovated lakefront home!
4 bedrooms, 7 beds, 2 bathrooms
20–25 Sept
4.95 out of 5 average rating, 39 reviews
Top guest favourite
Cabin in Harwinton
Beautiful Brook-side Log Cabin on 3 Private Acres
2 bedrooms, 2 queen beds, 1.5 bathrooms
1–6 Nov
4.97 out of 5 average rating, 113 reviews
Top guest favourite
Cabin in Norfolk
The Red Cabin-Secluded Getaway with backyard Brook
2 bedrooms, 2 beds, 1 bathroom
30 Oct – 4 Nov
4.99 out of 5 average rating, 124 reviews
Guest favourite
Home in Winsted
Serene Getaway in the Berkshires
4 bedrooms, 4 beds, 4 bathrooms
10–15 Sept
5.0 out of 5 average rating, 6 reviews
Guest favourite
Cottage in Barkhamsted
Cottage - 2 bdr - West Hill Lake w/ Private Beach
2 bedrooms, 3 beds, 1 bathroom
16–21 May
4.97 out of 5 average rating, 30 reviews
Top guest favourite
Home in Harwinton
1800’s Farmhouse in the hills of Litchfield County
4 bedrooms, 5 beds, 2 bathrooms
11–16 Sept
5.0 out of 5 average rating, 33 reviews
Top guest favourite
Home in Colebrook
Stunning Views of the Berkshire Foothills
3 bedrooms, 4 beds, 2.5 bathrooms
17–22 Sept
5.0 out of 5 average rating, 33 reviews
Top guest favourite
Home in Torrington
Country living at it's finest
2 bedrooms, 2 beds, 1 bathroom
28 Sept – 3 Oct
4.99 out of 5 average rating, 120 reviews
Guest favourite
Flat in Winsted
Getaway for a weekend! Close to Ski Sundown.
1 bedroom, 1 bed, 1 bathroom
13–18 Sept
4.9 out of 5 average rating, 147 reviews
Guest favourite
Cabin in Colebrook
Rustic Pond Cabin: Nature, Stars & Serenity
2 bedrooms, 2 beds, 1.5 bathrooms
20–25 Oct
4.95 out of 5 average rating, 129 reviews
Guest favourite
Home in Winchester
Bluebird School House
1 bedroom, 2 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Goshen
Halo Hollow Haus - Litchfield Lake & Ski Haven
3 bedrooms, 5 beds, 2 bathrooms
28 Sept – 3 Oct
4.92 out of 5 average rating, 53 reviews
Top guest favourite
Flat in Torrington
“The Clemons!” Central AC - 3 Beds - Main Level
3 bedrooms, 3 beds, 1.5 bathrooms
26–31 Oct
4.99 out of 5 average rating, 159 reviews
Guest favourite
Flat in Torrington
Modern/Private Five ★ /Hotel quality stay/1 BR Apt
1 bedroom, 1 queen bed, 1 bathroom
3–8 Dec
4.95 out of 5 average rating, 292 reviews