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Search results; Over 1,000 homes in Winchester

Top guest favourite
Farm stay in Winchester
LenMar Farm Country Stay near Lexington KY
2 bedrooms, 3 beds, 1 private bathroom
13–18 Jul
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4.94 out of 5 average rating, 190 reviews
Top guest favourite
Home in Winchester
Cozy Cottage
4.92 out of 5 average rating, 945 reviews, 1 bedroom, 1 bed, 1 bathroom
13–18 Sept
Guest favourite
Loft in Winchester
Stylish Loft 2Bdrm Winchester ky near Lexington
4.96 out of 5 average rating, 99 reviews, 2 bedrooms, 2 beds, 2 bathrooms
14–19 Jul
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
12–17 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
8–13 Jul
Top guest favourite
Home in Winchester
Country Refuge @ The Right Angle *Remote *Hot Tub
4.99 out of 5 average rating, 89 reviews, 2 bedrooms, 4 beds, 2 bathrooms
8–13 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
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
Farm stay in Winchester
Family Farm Winchester/Lexington 20 min.*Game Room
4.97 out of 5 average rating, 142 reviews, 4 bedrooms, 8 beds, 3 bathrooms
19–24 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
12–17 Jul
Guest favourite
Home in Winchester
Comfortable Bluegrass Living
5.0 out of 5 average rating, 12 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
27 Jul – 1 Aug
Guest favourite
Cabin in Winchester
Historic Cabin - Farm - Near RRG, Lex, local music
4.92 out of 5 average rating, 89 reviews, 2 bedrooms, 3 beds, 2 bathrooms
19–24 Jul
Top guest favourite
Cabin in Mount Sterling
The Honey Hut, Think of “ On Golden Pond"
4.97 out of 5 average rating, 295 reviews, 1 bedroom, 2 beds, 1 bathroom
12–17 Jul
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
Guest favourite
Cabin in Lexington
1800’s Historical Log Cabin Lexington KY
4.89 out of 5 average rating, 134 reviews, 2 bedrooms, 5 beds, 2.5 bathrooms
6–11 Aug
Top guest favourite
Home in Clay City
Mountain Retreat | Pool, Pond, Views & Wi-Fi
5.0 out of 5 average rating, 8 reviews, 3 bedrooms, 4 beds, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Home in Sharpsburg
Peaceful Kentucky Ranch
5.0 out of 5 average rating, 18 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
12–17 Jul
Top guest favourite
Home in Irvine
Pauline's Paradise
4.99 out of 5 average rating, 135 reviews, 2 bedrooms, 3 beds, 1 bathroom
3–8 Aug
Top guest favourite
Farm stay in Winchester
*2Rm Farm Cottage*King Bed*5min DT Winchester
5.0 out of 5 average rating, 94 reviews, 1 bedroom, 2 beds, 1 bathroom
19–24 Jul