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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
2–7 Aug
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4.97 out of 5 average rating, 223 reviews
Home in Winchester
Waterfront & Guest House Available in Winsted, CT!
5 bedrooms, 7 beds, 3 bathrooms
12–17 Aug
New place to stay
Guest favourite
Room in Barkhamsted
Sweet Suite in Lakefront Chalet-pvt bath
2 beds, 1 bathroom
2–7 Aug
4.88 out of 5 average rating, 159 reviews
Guest favourite
Flat in Winsted
Inn at Highland Lake: 1st Fl Suite w/ Dock
1 bedroom, 2 beds, 1 bathroom
1–6 Aug
4.89 out of 5 average rating, 47 reviews
Guest favourite
Flat in Winsted
Getaway for a weekend! Close to Ski Sundown.
1 bedroom, 1 bed, 1 bathroom
16–21 Aug
4.92 out of 5 average rating, 142 reviews
Top guest favourite
Home in Winchester
Highland Lakefront Retreat
4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
4.95 out of 5 average rating, 37 reviews
Top guest favourite
Room in Norfolk
Norfolk's Charming Suite in the heart of town
1 queen bed, 1 bathroom
2–7 Aug
4.94 out of 5 average rating, 145 reviews
Guest house in Winchester
Highland Lake Guest House | Private Waterfront
2 bedrooms, 4 beds, 1 bathroom
12–17 Aug
New place to stay
Superhost
Home in New Hartford
Sunset Pad. Lakefront for 2, private dock & SUPs.
1 bedroom, 1 king bed, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Cottage in Winsted
Cottage Ease.
2 bedrooms, 2 beds, 1 bathroom
17–22 Aug
4.93 out of 5 average rating, 54 reviews
Guest favourite
Home in Winsted
Winsted /Winchester House wifi high speed internet
4 bedrooms, 6 beds, 2 bathrooms
10–16 Aug
4.89 out of 5 average rating, 35 reviews
Superhost
Serviced apartment in Winsted
Haven at Highland lake
1 bedroom, 2 beds, 1 bathroom
23–28 Aug
4.87 out of 5 average rating, 174 reviews
Guest favourite
Tiny home in New Hartford
West Hill Outpost
1 queen bed, 1 bathroom
12–17 Aug
4.9 out of 5 average rating, 98 reviews
Home in Winchester
Spacious Lakefront Retreat w/Dock | Close to Town
5 bedrooms, 8 beds, 3 bathrooms
19–24 Aug
5.0 out of 5 average rating, 3 reviews
Room in Torrington
Large bedroom in quiet neighborhood
1 bed, 1 bathroom
2–7 Aug
Top guest favourite
Home in Winsted
Newly renovated lakefront home!
4 bedrooms, 7 beds, 2 bathrooms
31 Aug – 5 Sept
4.95 out of 5 average rating, 39 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
Flat in Torrington
Charming Private Apartment Near Downtown
2 bedrooms, 2 queen beds, 1 bathroom
2–7 Aug
5.0 out of 5 average rating, 6 reviews
Home in Winchester
NEW! Lakefront Retreat on Highland Lake
6 bedrooms, 10 beds, 2.5 bathrooms
9–14 Sept
New place to stay