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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
1–6 Aug
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4.92 out of 5 average rating, 91 reviews
Guest favourite
Home in Winchester
Cozy Cottage
1 bedroom, 1 queen bed
13–18 Sept
4.92 out of 5 average rating, 953 reviews
Top guest favourite
Guest house in Winchester
Carriage House Gardenside
1 bedroom, 1 king bed
1–6 Aug
4.96 out of 5 average rating, 121 reviews
Top guest favourite
Flat in Winchester
The Carriage Inn - 1-bdrm apt in historic downtown
1 bedroom, 1 queen bed
2–7 Aug
4.93 out of 5 average rating, 121 reviews
Guest favourite
Loft in Winchester
Stylish Loft 2Bdrm Winchester ky near Lexington
2 bedrooms, 2 beds
9–14 Aug
4.96 out of 5 average rating, 100 reviews
Guest favourite
Home in Winchester
Bloomfield Garden House
2 bedrooms, 2 beds
11–16 Aug
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Farm stay in Winchester
LenMar Farm Country Stay near Lexington KY
2 bedrooms, 3 beds
14–19 Sept
4.94 out of 5 average rating, 192 reviews
Guest favourite
Loft in Winchester
Artist’s Loft 2Bdr Winchester ky near Lexington
2 bedrooms, 2 king beds
3–8 Aug
5.0 out of 5 average rating, 51 reviews
Guest favourite
Home in Winchester
Comfortable Bluegrass Living
2 bedrooms, 3 beds
4–9 Aug
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Farm stay in Winchester
*2Rm Farm Cottage*King Bed*5min DT Winchester
1 bedroom, 2 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 97 reviews
Superhost
Flat in Winchester
RiverView 1 - Enjoy the view.
1 bedroom, 3 beds
16–21 Aug
4.79 out of 5 average rating, 68 reviews
Top guest favourite
Home in Winchester
Right Angle Country*Remote*Hot Tub~NO Cleaning FEE
2 bedrooms, 4 beds
3–8 Aug
4.99 out of 5 average rating, 90 reviews
Guest favourite
Home in Lexington
Charming Kentucky Stone House
2 bedrooms, 2 beds
8–13 Aug
4.9 out of 5 average rating, 71 reviews
Top guest favourite
Home in Mount Sterling
High Street Hideaway home atmosphere for relaxing
2 bedrooms, 2 queen beds
6–11 Aug
5.0 out of 5 average rating, 111 reviews
Guest favourite
Home in Mount Sterling
Five O’clock Somewhere
1 bedroom, 1 bed
2–7 Aug
5.0 out of 5 average rating, 31 reviews
Top guest favourite
Farm stay in Winchester
Family Farm Winchester/Lexington 20 min.*Game Room
4 bedrooms, 8 beds
30 Aug – 4 Sept
4.97 out of 5 average rating, 144 reviews
Top guest favourite
Guest suite in Lexington
The Gainesway Suite-Near UK, Hospitals, Keeneland
1 bedroom, 1 queen bed
1–6 Aug
5.0 out of 5 average rating, 279 reviews
Top guest favourite
Cabin in Mount Sterling
The Honey Hut, Think of “ On Golden Pond"
1 bedroom, 2 beds
9–14 Aug
4.97 out of 5 average rating, 298 reviews
Top guest favourite
Home in Richmond
Silo Mill
1 bedroom, 1 bed
6–11 Aug
4.96 out of 5 average rating, 51 reviews