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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
14–19 Sept
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4.94 out of 5 average rating, 192 reviews
Guest favourite
Loft in Winchester
Stylish Loft 2Bdrm Winchester ky near Lexington
4.96 out of 5 average rating, 100 reviews, 2 bedrooms, 2 beds, 2 bathrooms
9–14 Aug
Guest favourite
Home in Winchester
Cozy Cottage
4.92 out of 5 average rating, 952 reviews, 1 bedroom, 1 bed, 1 bathroom
13–18 Sept
Guest favourite
Loft in Winchester
Artist’s Loft 2Bdr Winchester ky near Lexington
5.0 out of 5 average rating, 51 reviews, 2 bedrooms, 2 beds, 2 bathrooms
3–8 Aug
Guest favourite
Guest house in Winchester
Carriage House on the Park
4.92 out of 5 average rating, 227 reviews, 1 bedroom, 1 bed, 1 bathroom
5–10 Aug
Guest favourite
Home in Winchester
Bloomfield Garden House
5.0 out of 5 average rating, 9 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
2–7 Aug
Guest favourite
Home in Winchester
Comfortable Bluegrass Living
5.0 out of 5 average rating, 14 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
4–9 Aug
Top guest favourite
Home in Winchester
Right Angle Country*Remote*Hot Tub~NO Cleaning FEE
4.99 out of 5 average rating, 90 reviews, 2 bedrooms, 4 beds, 2 bathrooms
3–8 Aug
Top guest favourite
Farm stay in Winchester
Family Farm Winchester/Lexington 20 min.*Game Room
4.97 out of 5 average rating, 144 reviews, 4 bedrooms, 8 beds, 3 bathrooms
30 Aug – 4 Sept
Superhost
Flat in Winchester
RiverView 1 - Enjoy the view.
4.79 out of 5 average rating, 68 reviews, 1 bedroom, 3 beds, 1 bathroom
16–21 Aug
Top guest favourite
Loft in Mount Sterling
One Bedroom apartment with full kitchen
4.98 out of 5 average rating, 64 reviews, 1 bedroom, 1 bed, 1 bathroom
4–9 Jan
Top guest favourite
Farm stay in Winchester
*2Rm Farm Cottage*King Bed*5min DT Winchester
5.0 out of 5 average rating, 97 reviews, 1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
Guest favourite
Cabin in Winchester
Historic Cabin - Farm - Near RRG, Lex, local music
4.92 out of 5 average rating, 91 reviews, 2 bedrooms, 3 beds, 2 bathrooms
1–6 Aug
Top guest favourite
Cottage in Lexington
Bluegrass Cottage;Pet Friendly.Horse Farm & Racing
4.97 out of 5 average rating, 91 reviews, 2 bedrooms, 3 beds, 1 bathroom
19–24 Aug
Top guest favourite
Flat in Richmond
Modern 2bd 2ba - Near I75, No Steps, Free Wifi
4.95 out of 5 average rating, 167 reviews, 2 bedrooms, 3 beds, 2 bathrooms
2–7 Aug
Top guest favourite
Home in Sharpsburg
Firethorn’s Hilltop Haven
4.96 out of 5 average rating, 27 reviews, 3 bedrooms, 3 beds, 2 bathrooms
16–21 Aug
Top guest favourite
Home in Stanton
Cozy Home Close to RRG Action
5.0 out of 5 average rating, 39 reviews, 3 bedrooms, 3 beds, 2 bathrooms
2–7 Aug
Top guest favourite
Cabin in Nicholasville
The Lodge at Marble Creek
4.98 out of 5 average rating, 46 reviews, 3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept