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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
23–28 Aug
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4.97 out of 5 average rating, 226 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
Top guest favourite
Home in Winchester
Highland Lakefront Retreat
4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
4.93 out of 5 average rating, 42 reviews
Home in Winchester
Waterfront & Guest House Available in Winsted, CT!
5 bedrooms, 7 beds, 3 bathrooms
18–23 Aug
New place to stay
Guest favourite
Home in Winchester
Bluebird School House
1 bedroom, 2 beds, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Tiny home in Litchfield
My Friend's Place
1 bedroom, 1 queen bed, 1 bathroom
28 Aug – 2 Sept
4.94 out of 5 average rating, 129 reviews
Guest favourite
Tiny home in New Marlborough
Bedroom Forest View I Sauna I Fire-pit I Trails
2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
4.94 out of 5 average rating, 191 reviews
Top guest favourite
Room in Norfolk
Norfolk's Charming Suite in the heart of town
1 queen bed, 1 bathroom
26–31 Aug
4.94 out of 5 average rating, 146 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
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
Guest suite in Torrington
Garden Retreat in New England Near Lake & Trails
1 bedroom, 1 bathroom
23–28 Aug
4.81 out of 5 average rating, 131 reviews
Top guest favourite
Cabin in Litchfield County
Blackberry Cottage
1 bedroom, 3 beds, 1 bathroom
23–28 Aug
4.94 out of 5 average rating, 155 reviews
Guest favourite
Flat in Winsted
Getaway for a weekend! Close to Ski Sundown.
1 bedroom, 1 bed, 1 bathroom
31 Aug – 5 Sept
4.92 out of 5 average rating, 143 reviews
Guest favourite
Cottage in New Hartford
Cozy West Hill Lake Cottage Retreat
1 bedroom, 2 double beds, 1 bathroom
24–29 Aug
4.88 out of 5 average rating, 16 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
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 house in Barkhamsted
Farmington River Carriage House Pleasant Valley CT
2 bedrooms, 3 beds, 1 bathroom
14–19 Sept
4.91 out of 5 average rating, 121 reviews
Guest favourite
Cabin in New Hartford
West Hill Cabin
3 bedrooms, 4 beds, 2 bathrooms
11–16 Sept
4.97 out of 5 average rating, 75 reviews
Guest favourite
Treehouse in New Marlborough
Berkshire Treehouse Retreat
3 bedrooms, 4 beds, WC
23–28 Aug
4.91 out of 5 average rating, 171 reviews