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Search results; Over 1,000 homes in Winchester

Descriptions are based on details hosts provide
Guest favourite
Cabin in Winchester
Historic Cabin - Farm - Near RRG, Lex, local music
2 bedrooms, 3 beds, 2 private bathrooms
19–24 Jul
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4.92 out of 5 average rating, 89 reviews
Guest favourite
Loft in Winchester
New York-style loft, historic renovation downtown
4.96 out of 5 average rating, 100 reviews, 2 bedrooms, 2 beds, 2 bathrooms
15–20 Jul
Top guest favourite
Home in Winchester
Cozy Cottage
4.92 out of 5 average rating, 947 reviews, 1 bedroom, 1 bed, 1 bathroom
13–18 Sept
Guest favourite
Loft in Winchester
Artist’s Loft 2Bdr Winchester ky near Lexington
5.0 out of 5 average rating, 50 reviews, 2 bedrooms, 2 beds, 2 bathrooms
16–21 Jul
Top guest favourite
Farm stay in Winchester
7th-generation farm with a game room
4.97 out of 5 average rating, 142 reviews, 4 bedrooms, 8 beds, 3 bathrooms
19–24 Jul
Guest favourite
Guest house in Winchester
Carriage House on the Park
4.92 out of 5 average rating, 226 reviews, 1 bedroom, 1 bed, 1 bathroom
15–20 Jul
Top guest favourite
Home in Winchester
Secluded homestead with a hot tub
4.99 out of 5 average rating, 89 reviews, 2 bedrooms, 4 beds, 2 bathrooms
15–20 Jul
Top guest favourite
Flat in Winchester
The Carriage Inn - 1-bdrm apt in historic downtown
4.93 out of 5 average rating, 121 reviews, 1 bedroom, 1 bed, 1 bathroom
15–20 Jul
Guest favourite
Home in Winchester
Bloomfield Garden House
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 2 beds, 2 bathrooms
11–16 Aug
Top guest favourite
Farm stay in Winchester
LenMar Farm Country Stay near Lexington KY
4.94 out of 5 average rating, 190 reviews, 2 bedrooms, 3 beds, 1 bathroom
14–19 Sept
Top guest favourite
Farm stay in Winchester
Farm cottage on an 1803 family farm
5.0 out of 5 average rating, 94 reviews, 1 bedroom, 2 beds, 1 bathroom
19–24 Jul
Guest favourite
Home in Winchester
Comfortable Bluegrass Living
5.0 out of 5 average rating, 13 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
27 Jul – 1 Aug
Top guest favourite
Loft in Mount Sterling
Spacious loft 2 blocks from downtown
4.98 out of 5 average rating, 64 reviews, 1 bedroom, 1 bed, 1 bathroom
4–9 Jan
Guest favourite
Home in Mount Sterling
Bourbon on the Hill
4.97 out of 5 average rating, 34 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Jul
Top guest favourite
Cabin in Mount Sterling
The Honey Hut, Think of “ On Golden Pond"
4.97 out of 5 average rating, 296 reviews, 1 bedroom, 2 beds, 1 bathroom
15–20 Jul
Superhost
Flat in Winchester
RiverView 1 - Enjoy the view.
4.79 out of 5 average rating, 67 reviews, 1 bedroom, 3 beds, 1 bathroom
16–21 Aug
Guest favourite
Cabin in Richmond
Secluded riverfront cabin with a fire pit
4.94 out of 5 average rating, 34 reviews, 3 bedrooms, 3 beds, 2 bathrooms
23–28 Jul
Guest favourite
Townhouse in Lexington
Bounce to Hamburg/I-75/St. Joe E
4.94 out of 5 average rating, 80 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
19–24 Jul
Home in Frenchburg
Hot tub and fire pit by a creek
New place to stay, 3 bedrooms, 4 beds, 2 bathrooms
19–24 Jul