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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, 188 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
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
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
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
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
Home in Winchester
Comfortable Bluegrass Living
5.0 out of 5 average rating, 12 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
1–6 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
Top guest favourite
Home in Winchester
Country Refuge @ The Right Angle *Remote *Hot Tub
4.99 out of 5 average rating, 88 reviews, 2 bedrooms, 4 beds, 2 bathrooms
5–10 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
Superhost
Flat in Mount Sterling
Pawplex
4.94 out of 5 average rating, 17 reviews, 1 bedroom, 1 bed, 1 bathroom
3–8 Jul
Guest favourite
Home in Winchester
Hikers’ Friend
4.78 out of 5 average rating, 9 reviews, 1 bedroom, 2 beds, 1 bathroom
1–6 Jul
Top guest favourite
Home in Richmond
Near to EKU and just minutes from I-75
4.97 out of 5 average rating, 180 reviews, 1 bedroom, 1 bed, 1 bathroom
9–14 Aug
Top guest favourite
Guest house in Lexington
Conveniently located to UK, Keeneland and Hamburg
4.97 out of 5 average rating, 94 reviews, 3 bedrooms, 6 beds, 2 bathrooms
1–6 Nov
Top guest favourite
Home in Richmond
Walnut Creek Retreat - King Suit - Waterfall
4.99 out of 5 average rating, 71 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
4–9 Jul
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
Home in Richmond
Blue Skies Farm - King Suite - Beautiful Views
4.87 out of 5 average rating, 23 reviews, 4 bedrooms, 6 beds, 3 bathrooms
5–10 Jul
Top guest favourite
Home in Richmond
Newly Built Town & Country
4.99 out of 5 average rating, 127 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
25–30 Jul
Top guest favourite
Home in Richmond
Silo Mill
4.95 out of 5 average rating, 43 reviews, 1 bedroom, 1 bed, 1 bathroom
15–20 Jul