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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
Home in Winchester
Cozy Cottage
1 bedroom, 1 queen bed, 1 bathroom
13–18 Sept
4.92 out of 5 average rating, 953 reviews
Guest favourite
Guest house in Winchester
Carriage House on the Park
1 bedroom, 1 queen bed, 1 bathroom
12–17 Aug
4.92 out of 5 average rating, 227 reviews
Top guest favourite
Flat in Winchester
The Carriage Inn - 1-bdrm apt in historic downtown
1 bedroom, 1 queen bed, 1 bathroom
9–14 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, 2 bathrooms
9–14 Aug
4.96 out of 5 average rating, 100 reviews
Guest favourite
Home in Winchester
Bloomfield Garden House
2 bedrooms, 2 beds, 2 bathrooms
11–16 Aug
5.0 out of 5 average rating, 9 reviews
Guest favourite
Loft in Winchester
Artist’s Loft 2Bdr Winchester ky near Lexington
2 bedrooms, 2 king beds, 2 bathrooms
3–8 Aug
5.0 out of 5 average rating, 51 reviews
Guest favourite
Home in Winchester
Comfortable Bluegrass Living
2 bedrooms, 3 beds, 1.5 bathrooms
4–9 Aug
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Home in Winchester
Right Angle Country*Remote*Hot Tub~NO Cleaning FEE
2 bedrooms, 4 beds, 2 bathrooms
9–14 Aug
4.99 out of 5 average rating, 91 reviews
Top guest favourite
Farm stay in Winchester
*2Rm Farm Cottage*King Bed*5min DT Winchester
1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 98 reviews
Superhost
Flat in Winchester
RiverView 1 - Enjoy the view.
1 bedroom, 3 beds, 1 bathroom
16–21 Aug
4.79 out of 5 average rating, 68 reviews
Guest favourite
Cabin in Winchester
Historic Cabin - Farm - Near RRG, Lex, local music
2 bedrooms, 3 beds, 2 bathrooms
9–14 Aug
4.92 out of 5 average rating, 91 reviews
Top guest favourite
Farm stay in Winchester
Family Farm Winchester/Lexington 20 min.*Game Room
4 bedrooms, 8 beds, 3 bathrooms
30 Aug – 4 Sept
4.97 out of 5 average rating, 144 reviews
Guest favourite
Home in Lexington
Cozy 1-bedroom in Lexington
1 bedroom, 1 bed, 1 bathroom
9–14 Aug
4.88 out of 5 average rating, 117 reviews
Guest favourite
Townhouse in Lexington
Bounce to Hamburg/I-75/St. Joe E
2 bedrooms, 2 beds, 2.5 bathrooms
5–10 Aug
4.94 out of 5 average rating, 82 reviews
Top guest favourite
Home in Richmond
Silo Mill
1 bedroom, 1 bed, 1 bathroom
6–11 Aug
4.96 out of 5 average rating, 52 reviews
Townhouse in Lexington
The Thoroughbred Retreat
2 bedrooms, 2 beds, 1.5 bathrooms
9–14 Aug
4.75 out of 5 average rating, 40 reviews
Guest favourite
Flat in Mount Sterling
Pawplex
1 bedroom, 1 queen bed, 1 bathroom
7–12 Aug
4.96 out of 5 average rating, 25 reviews
Top guest favourite
Barn in Paris
Horse & Flower Farm Barn Loft
3 bedrooms, 3 beds, 1 bathroom
3–8 Aug
4.96 out of 5 average rating, 98 reviews