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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
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, 178 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
Guest favourite
Flat in Winsted
2nd Floor The Inn at Highland Lake
3 bedrooms, 5 beds, 1 bathroom
24–29 Aug
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
23–28 Aug
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
21–26 Aug
4.92 out of 5 average rating, 25 reviews
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
Top guest favourite
Home in Winchester
Highland Lakefront Retreat
4 bedrooms, 5 beds, 2 bathrooms
2–7 Oct
4.93 out of 5 average rating, 42 reviews
Top guest favourite
Cottage in Winsted
Cottage Ease.
2 bedrooms, 2 beds, 1 bathroom
29 Aug – 3 Sept
4.93 out of 5 average rating, 58 reviews
Superhost
Cabin in New Hartford
West Hill Cottage-stroll to pristine beach
3 bedrooms, 4 beds, 1.5 bathrooms
23–28 Aug
New place to stay
Top guest favourite
Home in Barkhamsted
3BR Family friendly home in Riverton paradise
3 bedrooms, 5 beds, 2 bathrooms
12–17 Sept
4.95 out of 5 average rating, 38 reviews
Guest favourite
Home in New Hartford
Modern Farmhouse
3 bedrooms, 3 queen beds, 1.5 bathrooms
8–13 Sept
4.89 out of 5 average rating, 158 reviews
Top guest favourite
Home in Litchfield County
70's Retro House
2 bedrooms, 2 queen beds, 2 bathrooms
25–30 Aug
4.96 out of 5 average rating, 27 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
Top guest favourite
Tiny home in Litchfield
My Friend's Place
1 bedroom, 1 queen bed, 1 bathroom
13–18 Sept
4.94 out of 5 average rating, 129 reviews
Top guest favourite
Home in Colebrook
Norbrook Farm ~ Rustic farmhouse w/ pond & trails
3 bedrooms, 4 beds, 2 bathrooms
10–15 Sept
4.99 out of 5 average rating, 248 reviews
Top guest favourite
Room in Simsbury
Forest-View Room + Private Bath
1 queen bed, 1 bathroom
30 Aug – 4 Sept
4.96 out of 5 average rating, 430 reviews
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
Guest favourite
Tiny home in New Marlborough
Bedroom Forest View I Sauna I Fire-pit I Trails
2 bedrooms, 2 beds, 1 bathroom
22–27 Sept
4.94 out of 5 average rating, 191 reviews