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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
12–17 Jul
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4.89 out of 5 average rating, 168 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
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
Home in Winchester
Spacious Lakefront Retreat w/Dock | Close to Town
5 bedrooms, 8 beds, 3 bathrooms
7–12 Jul
Guest favourite
Flat in Winsted
Getaway for a weekend! Close to Ski Sundown.
4.91 out of 5 average rating, 140 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
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
Superhost
Home in Winsted
Renovated lake house, just steps to the water.
4.81 out of 5 average rating, 59 reviews, 3 bedrooms, 4 beds, 2 bathrooms
26–31 Jul
Guest favourite
Home in Winsted
Lake House- Great for Families
4.98 out of 5 average rating, 64 reviews, 5 bedrooms, 7 beds, 3.5 bathrooms
12–18 Aug
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
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
Guest favourite
Home in Winsted
Spacious & serene house in Berkshires
4.89 out of 5 average rating, 19 reviews, 4 bedrooms, 5 beds, 3.5 bathrooms
28 Jul – 2 Aug
Home in Winsted
Lakefront Escape on Highland
5 bedrooms, 7 beds, 4 bathrooms
27 Jul – 1 Aug
Top guest favourite
Home in Torrington
Clean & Quiet Home| Enclosed 3 Season Porch & Deck
5.0 out of 5 average rating, 58 reviews, 3 bedrooms, 3 beds, 1 bathroom
5–10 Jul
Guest favourite
Flat in Winchester
Gateway to the Berkshires
4.91 out of 5 average rating, 422 reviews, 1 bedroom, 5 beds, 1 bathroom
7–12 Sept
Top guest favourite
Home in Winsted
Luxury Highland Lake Waterfront
5.0 out of 5 average rating, 33 reviews, 7 bedrooms, 11 beds, 4 bathrooms
8–13 Sept
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
Home in Colebrook
Riverton Retreat | Home on the Farmington River
New place to stay, 3 bedrooms, 4 beds, 1.5 bathrooms
12–17 Jul
Flat in Torrington
Charming Private Apartment Near Downtown
New place to stay, 2 bedrooms, 2 beds, 1 bathroom
11–16 Jul