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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
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
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
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
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
Flat in Mount Sterling
Historic 2-Bedroom Apartment in Downtown
4.97 out of 5 average rating, 91 reviews, 2 bedrooms, 2 beds, 1 bathroom
12–17 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
Flat in Mount Sterling
No-Frills Main Street Stay | Upstairs Private Apt
New place to stay, 1 bedroom, 1 bed, 1 bathroom
12–17 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
Guest favourite
Farm stay in Winchester
The Winchester Retreat
4.83 out of 5 average rating, 157 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 May
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
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
Top guest favourite
Home in Richmond
Blue Skies Farm - King Suite - Beautiful Views
4.88 out of 5 average rating, 24 reviews, 4 bedrooms, 6 beds, 3 bathrooms
9–14 Jul
Guest favourite
Flat in Lexington
*One Bed Apartment|One Mile to Rupp Arena*
4.87 out of 5 average rating, 257 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul
Top guest favourite
Home in Richmond
Newly Built Town & Country
4.99 out of 5 average rating, 130 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
25–30 Jul