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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
16–21 Aug
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4.97 out of 5 average rating, 226 reviews
Home in Winchester
Waterfront & Guest House Available in Winsted, CT!
5 bedrooms, 7 beds, 3 bathrooms
12–17 Aug
New place to stay
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, 177 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, 41 reviews
Guest favourite
Flat in Winsted
2nd Floor The Inn at Highland Lake
3 bedrooms, 5 beds, 1 bathroom
11–16 Aug
4.91 out of 5 average rating, 65 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, 130 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, 189 reviews
Flat in Canton
New bright, spotless apartment in N. Canton
2 bedrooms, 2 beds, 1 bathroom
17–22 Sept
5.0 out of 5 average rating, 3 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, 120 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
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
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
Flat in Torrington
Charming Private Apartment Near Downtown
2 bedrooms, 2 queen beds, 1 bathroom
15–20 Aug
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Room in Norfolk
Maple House, Birch Room
1 queen bed, 1 bathroom
16–21 Aug
4.98 out of 5 average rating, 56 reviews
Guest favourite
Villa in Winsted
Waterfront Litchfield Hills 1-bdrm Old Mill villa
1 bedroom, 1 bed, 1.5 bathrooms
11–16 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Cabin in Litchfield County
Blackberry Cottage
1 bedroom, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.93 out of 5 average rating, 152 reviews
Guest favourite
Home in Norfolk
entire farm style house
2 bedrooms, 4 beds, 1 bathroom
17–23 Aug
4.91 out of 5 average rating, 11 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
Superhost
Cabin in New Hartford
West Hill Cottage-stroll to pristine beach
3 bedrooms, 4 beds, 1.5 bathrooms
17–22 Aug
New place to stay