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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, 90 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
18–23 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
18–23 Jul
Top guest favourite
Home in Winchester
Cozy Cottage
4.92 out of 5 average rating, 949 reviews, 1 bedroom, 1 bed, 1 bathroom
13–18 Sept
Top guest favourite
Home in Winchester
Right Angle Country*Remote*Hot Tub~NO Cleaning FEE
4.99 out of 5 average rating, 89 reviews, 2 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
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
18–23 Jul
Top guest favourite
Farm stay in Winchester
LenMar Farm Country Stay near Lexington KY
4.94 out of 5 average rating, 190 reviews, 2 bedrooms, 3 beds, 1 bathroom
14–19 Sept
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
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
5–10 Aug
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
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
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
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
Guest favourite
Home in Lexington
The Coffee House
5.0 out of 5 average rating, 71 reviews, 3 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
Guest favourite
Home in Mount Sterling
Bourbon on the Hill
4.97 out of 5 average rating, 34 reviews, 1 bedroom, 1 bed, 1 bathroom
18–23 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
26–31 Jul
Top guest favourite
Cabin in Mount Sterling
The Honey Hut, Think of “ On Golden Pond"
4.97 out of 5 average rating, 296 reviews, 1 bedroom, 2 beds, 1 bathroom
9–14 Aug
Superhost
Cabin in Winston
Social Distance/127 Private Acres -Hot Tub -Wi-Fi
New place to stay, 2 bedrooms, 2 beds, 1 bathroom
27 Jul – 1 Aug
Guest favourite
Home in Clay City
Hidden Hideaway
4.8 out of 5 average rating, 5 reviews, 2 bedrooms, 2 beds, 1 bathroom
27 Jul – 1 Aug