Search results; Over 1,000 homes in Winchester

Guest favourite
Flat in Winchester
Gateway to the Berkshires
1 bedroom, 5 beds, 1 private bathroom
31 Aug – 5 Sept
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4.9 out of 5 average rating, 421 reviews
Top guest favourite
Home in Winchester
Highland Lakefront Retreat
4.94 out of 5 average rating, 32 reviews, 4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
Guest favourite
Flat in Winsted
2nd Floor The Inn at Highland Lake
4.91 out of 5 average rating, 65 reviews, 3 bedrooms, 5 beds, 1 bathroom
5–10 Jul
Top guest favourite
Guest suite in Winchester
Private Suite 2 Bedroom Deck Lake Views
4.97 out of 5 average rating, 213 reviews, 2 bedrooms, 2 beds, 1 bathroom
11–16 Jul
Home in Winchester
Spacious Lakefront Retreat w/Dock | Close to Town
5 bedrooms, 8 beds, 3 bathrooms
7–12 Jul
Guest favourite
Villa in Winsted
Waterfront Litchfield Hills 1-bdrm Old Mill villa
5.0 out of 5 average rating, 5 reviews, 1 bedroom, 1 bed, 1.5 bathrooms
1–6 Jul
Top guest favourite
Home in Winsted
Newly renovated lakefront home!
4.95 out of 5 average rating, 38 reviews, 4 bedrooms, 7 beds, 2 bathrooms
18–23 Jul
Top guest favourite
Home in Colebrook
Norbrook Farm ~ Rustic farmhouse w/ pond & trails
4.99 out of 5 average rating, 244 reviews, 3 bedrooms, 4 beds, 2 bathrooms
21–26 Jul
Guest favourite
Cottage in Winsted
Cottage Ease.
4.93 out of 5 average rating, 54 reviews, 2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
Top guest favourite
Tiny home in Litchfield
My Friend's Place
4.96 out of 5 average rating, 112 reviews, 1 bedroom, 1 bed, 1 bathroom
15–20 Aug
Top guest favourite
Flat in Torrington
“The Clemons!” Central AC - 3 Beds - Main Level
4.99 out of 5 average rating, 152 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
16–21 Aug
Home in Torrington
Enjoy the NW Hills, then relax by the river…
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 4 beds, 2 bathrooms
26–31 Jul
Guest favourite
Cottage in Barkhamsted
Cottage - 2 bdr - West Hill Lake w/ Private Beach
4.97 out of 5 average rating, 30 reviews, 2 bedrooms, 3 beds, 1 bathroom
15–20 Aug
Top guest favourite
Guest house in Litchfield
The Cottage @ 228 Maple
5.0 out of 5 average rating, 34 reviews, 3 bedrooms, 3 beds, 2 bathrooms
13–18 Jul
Top guest favourite
Farm stay in West Simsbury
Flamig Farm Staycation
4.96 out of 5 average rating, 549 reviews, 2 bedrooms, 4 beds, 1 bathroom
20–25 Sept
Guest suite in Torrington
Garden Retreat in New England Near Lake & Trails
4.8 out of 5 average rating, 119 reviews, 1 bedroom, 1 bathroom
16–21 Aug
Guest favourite
Cottage in Winchester
Winsted/Highland Lake/Direct Waterfront/Immaculate
4.97 out of 5 average rating, 75 reviews, 3 bedrooms, 8 beds, 2 bathrooms
22–27 Aug
Top guest favourite
Home in Torrington
Country living at it's finest
4.99 out of 5 average rating, 114 reviews, 2 bedrooms, 2 beds, 1 bathroom
28 Jul – 2 Aug
Guest favourite
Cottage in Winsted
Waterfront Cottage at Highland Lake w/dock
5.0 out of 5 average rating, 17 reviews, 2 bedrooms, 4 beds, 2.5 bathrooms
31 Aug – 5 Sept