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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
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4.92 out of 5 average rating, 89 reviews
Top guest favourite
Home in Winchester
Cozy Cottage
4.92 out of 5 average rating, 943 reviews, 1 bedroom, 1 bed, 1 bathroom
20–25 Aug
Guest favourite
Loft in Winchester
Artist’s Loft 2Bdr Winchester ky near Lexington
5.0 out of 5 average rating, 49 reviews, 2 bedrooms, 2 beds, 2 bathrooms
12–17 Jul
Guest favourite
Home in Winchester
Bloomfield Garden House
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 2 beds, 2 bathrooms
1–6 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
3–8 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
5–10 Jul
Top guest favourite
Farm stay in Winchester
LenMar Farm Country Stay near Lexington KY
4.94 out of 5 average rating, 188 reviews, 2 bedrooms, 3 beds, 1 bathroom
13–18 Jul
Top guest favourite
Flat in Winchester
The Carriage Inn - 1-bdrm apt in historic downtown
4.93 out of 5 average rating, 119 reviews, 1 bedroom, 1 bed, 1 bathroom
7–12 Jul
Superhost
Flat in Mount Sterling
Pawplex
4.94 out of 5 average rating, 17 reviews, 1 bedroom, 1 bed, 1 bathroom
5–10 Jul
Top guest favourite
Farm stay in Winchester
Family Farm Winchester/Lexington 20 min.*Game Room
4.97 out of 5 average rating, 141 reviews, 4 bedrooms, 8 beds, 3 bathrooms
19–24 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
2–7 Jul
Top guest favourite
Cabin in Mount Sterling
The Honey Hut, Think of “ On Golden Pond"
4.97 out of 5 average rating, 293 reviews, 1 bedroom, 2 beds, 1 bathroom
12–17 Jul
Top guest favourite
Home in Winchester
Peacock Ranch House - Lexington and Winchester
5.0 out of 5 average rating, 33 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
1–6 Jul
Top guest favourite
Home in Mount Sterling
Five O’clock Somewhere
5.0 out of 5 average rating, 26 reviews, 1 bedroom, 1 bed, 1 bathroom
5–10 Jul
Top guest favourite
Cabin in Nicholasville
The Lodge at Marble Creek
4.98 out of 5 average rating, 40 reviews, 3 bedrooms, 4 beds, 2 bathrooms
16–21 Jul
Home in Lexington
Country cottage in the heart of the Bluegrass
4.92 out of 5 average rating, 24 reviews, 3 bedrooms, 3 beds, 1 bathroom
6–11 Jul
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
Tiny home in Richmond
The Stepping Stone Ranch
4.96 out of 5 average rating, 162 reviews, 3 bedrooms, 3 beds, 2 bathrooms
1–6 Jul
Top guest favourite
Cottage in Clay City
Enjoy tranquility or adventure in upscale cottage
4.98 out of 5 average rating, 138 reviews, 1 bedroom, 3 beds, 1.5 bathrooms
5–10 Jul