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Search results; Over 1,000 homes in Winchester

Guest favourite
Cabin in Winchester
Historic Cabin - Farm - Near RRG, Lex, local music
2 bedrooms, 3 beds, 2 private bathrooms
19–24 Jul
,
4.92 out of 5 average rating, 89 reviews
Top guest favourite
Home in Winchester
Cozy Cottage
1 bedroom, 1 queen bed, 1 bathroom
27 Jul – 1 Aug
4.92 out of 5 average rating, 945 reviews
Guest favourite
Loft in Winchester
Artist’s Loft 2Bdr Winchester ky near Lexington
2 bedrooms, 2 king beds, 2 bathrooms
12–17 Jul
5.0 out of 5 average rating, 50 reviews
Guest favourite
Loft in Winchester
Stylish Loft 2Bdrm Winchester ky near Lexington
2 bedrooms, 2 beds, 2 bathrooms
14–19 Jul
4.96 out of 5 average rating, 99 reviews
Top guest favourite
Farm stay in Winchester
LenMar Farm Country Stay near Lexington KY
2 bedrooms, 3 beds, 1 bathroom
13–18 Jul
4.94 out of 5 average rating, 190 reviews
Top guest favourite
Flat in Winchester
The Carriage Inn - 1-bdrm apt in historic downtown
1 bedroom, 1 queen bed, 1 bathroom
9–14 Jul
4.93 out of 5 average rating, 121 reviews
Top guest favourite
Home in Winchester
Country Refuge @ The Right Angle *Remote *Hot Tub
2 bedrooms, 4 beds, 2 bathrooms
9–14 Jul
4.99 out of 5 average rating, 89 reviews
Guest favourite
Home in Winchester
Bloomfield Garden House
2 bedrooms, 2 beds, 2 bathrooms
11–16 Aug
5.0 out of 5 average rating, 7 reviews
Guest favourite
Guest house in Winchester
Carriage House on the Park
1 bedroom, 1 queen bed, 1 bathroom
15–20 Jul
4.92 out of 5 average rating, 226 reviews
Top guest favourite
Farm stay in Winchester
Family Farm Winchester/Lexington 20 min.*Game Room
4 bedrooms, 8 beds, 3 bathrooms
19–24 Jul
4.97 out of 5 average rating, 142 reviews
Guest favourite
Home in Winchester
Comfortable Bluegrass Living
2 bedrooms, 3 beds, 1.5 bathrooms
27 Jul – 1 Aug
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Cabin in Mount Sterling
The Honey Hut, Think of “ On Golden Pond"
1 bedroom, 2 beds, 1 bathroom
12–17 Jul
4.97 out of 5 average rating, 295 reviews
Guest favourite
Home in Mount Sterling
Bourbon on the Hill
1 bedroom, 1 bed, 1 bathroom
16–21 Jul
4.97 out of 5 average rating, 34 reviews
Superhost
Flat in Winchester
RiverView 1 - Enjoy the view.
1 bedroom, 3 beds, 1 bathroom
12–17 Jul
4.79 out of 5 average rating, 67 reviews
Guest favourite
Cabin in Lexington
1800’s Historical Log Cabin Lexington KY
2 bedrooms, 5 beds, 2.5 bathrooms
6–11 Aug
4.89 out of 5 average rating, 134 reviews
Flat in Mount Sterling
No-Frills Main Street Stay | Upstairs Private Apt
1 bedroom, 1 king bed, 1 bathroom
12–17 Jul
New place to stay
Top guest favourite
Home in Clay City
Mountain Retreat | Pool, Pond, Views & Wi-Fi
3 bedrooms, 4 beds, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Farm stay in Winchester
*2Rm Farm Cottage*King Bed*5min DT Winchester
1 bedroom, 2 beds, 1 bathroom
19–24 Jul
5.0 out of 5 average rating, 94 reviews
Top guest favourite
Home in Sharpsburg
Peaceful Kentucky Ranch
3 bedrooms, 3 beds, 2.5 bathrooms
12–17 Jul
5.0 out of 5 average rating, 18 reviews