filters

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
9–14 Aug
,
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, 176 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, 36 reviews
Guest favourite
Cabin in Canaan
Secret Mountain Cabin/Catskills Views/100-Acres
1 bedroom, 1 double bed, 1 bathroom
23–28 Aug
4.95 out of 5 average rating, 41 reviews
Top guest favourite
Guest suite in Norfolk
The Nest at Lovers Lane
2 bedrooms, 5 beds, 1 bathroom
16–21 Aug
4.99 out of 5 average rating, 67 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, 40 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
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, 128 reviews
Guest favourite
Villa in Winsted
Waterfront Litchfield Hills 1-bdrm Old Mill villa
1 bedroom, 1 bed, 1.5 bathrooms
7–12 Aug
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in New Hartford
Modern Farmhouse
3 bedrooms, 3 queen beds, 1.5 bathrooms
10–15 Aug
4.89 out of 5 average rating, 158 reviews
Home in Winchester
Spacious Lakefront Retreat w/Dock | Close to Town
5 bedrooms, 8 beds, 3 bathrooms
16–21 Aug
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
7–12 Sept
4.91 out of 5 average rating, 120 reviews
Top guest favourite
Room in Norfolk
Maple House, Birch Room
1 queen bed, 1 bathroom
9–14 Aug
4.98 out of 5 average rating, 55 reviews
Guest favourite
Cottage in New Hartford
Cozy West Hill Lake Cottage Retreat
1 bedroom, 2 double beds, 1 bathroom
24–29 Aug
4.87 out of 5 average rating, 15 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, 151 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
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, 187 reviews
Home in Winchester
Bluebird School House
1 bedroom, 2 beds, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 4 reviews