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Search results; Over 1,000 homes in Winsted, Winchester

Guest favourite
Cottage in Winsted
Waterfront Cottage at Highland Lake w/dock
2 bedrooms, 4 beds, 2.5 private bathrooms
1–6 May
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5.0 out of 5 average rating, 17 reviews
Guest favourite
Flat in Winsted
Getaway for a weekend! Close to Ski Sundown.
1 bedroom, 1 bed, 1 bathroom
7–12 Sept
4.92 out of 5 average rating, 144 reviews
Superhost
Serviced apartment in Winsted
Haven at Highland lake
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
4.87 out of 5 average rating, 178 reviews
Guest favourite
Flat in Winsted
2nd Floor The Inn at Highland Lake
3 bedrooms, 5 beds, 1 bathroom
7–12 Sept
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
1–6 Sept
4.97 out of 5 average rating, 227 reviews
Guest favourite
Home in Winsted
Spacious & serene house in Berkshires
4 bedrooms, 5 beds, 3.5 bathrooms
1–6 Sept
4.92 out of 5 average rating, 25 reviews
Top guest favourite
Room in Norfolk
Maple House, Birch Room
1 queen bed, 1 bathroom
1–6 Sept
4.98 out of 5 average rating, 56 reviews
Top guest favourite
Home in Winsted
Newly renovated lakefront home!
4 bedrooms, 7 beds, 2 bathrooms
1–6 Sept
4.95 out of 5 average rating, 39 reviews
Top guest favourite
Cottage in Winsted
Cottage Ease.
2 bedrooms, 2 beds, 1 bathroom
11–16 Sept
4.93 out of 5 average rating, 58 reviews
Top guest favourite
Home in Winchester
Highland Lakefront Retreat
4 bedrooms, 5 beds, 2 bathrooms
27 Sept – 2 Oct
4.93 out of 5 average rating, 43 reviews
Top guest favourite
Home in Winsted
Luxury Highland Lake Waterfront
7 bedrooms, 11 beds, 4 bathrooms
8–13 Sept
5.0 out of 5 average rating, 36 reviews
Superhost
Cabin in New Hartford
West Hill Cottage-stroll to pristine beach
3 bedrooms, 4 beds, 1.5 bathrooms
1–6 Sept
New place to stay
Top guest favourite
Flat in Canton
New bright, spotless apartment in N. Canton
2 bedrooms, 2 beds, 1 bathroom
21–26 Sept
5.0 out of 5 average rating, 5 reviews
Superhost
Room in New Hartford
Suite 3 The West End Retreat, New Hartford, CT
1 queen bed, 1 bathroom
1–6 Sept
4.82 out of 5 average rating, 11 reviews
Guest favourite
Home in Winsted
Serene Getaway in the Berkshires
4 bedrooms, 4 beds, 4 bathrooms
1–6 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Room in Norfolk
Maple House, Oak Room
1 queen bed, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 42 reviews
Home in Winchester
Spacious Lakefront Retreat w/Dock | Close to Town
5 bedrooms, 8 beds, 3 bathrooms
8–13 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Room in Barkhamsted
Sweet Suite in Lakefront Chalet-pvt bath
2 beds, 1 bathroom
1–6 Sept
4.88 out of 5 average rating, 159 reviews
Top guest favourite
Farm stay in West Simsbury
Flamig Farm Staycation
2 bedrooms, 4 beds, 1 bathroom
20–25 Sept
4.96 out of 5 average rating, 555 reviews