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Search results; Over 1,000 homes in Winchester

Top guest favourite
Home in Winchester
Cozy Cottage
1 bedroom, 1 bed, 1 private bathroom
14–19 Sept
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4.92 out of 5 average rating, 960 reviews
Guest favourite
Guest house in Winchester
Carriage House on the Park
1 bedroom, 1 queen bed, 1 bathroom
26–31 Aug
4.92 out of 5 average rating, 229 reviews
Guest favourite
Loft in Winchester
Stylish Loft 2Bdrm Winchester ky near Lexington
2 bedrooms, 2 beds, 2 bathrooms
20–25 Aug
4.96 out of 5 average rating, 102 reviews
Guest favourite
Loft in Winchester
Artist’s Loft 2Bdr Winchester ky near Lexington
2 bedrooms, 2 king beds, 2 bathrooms
21–26 Aug
5.0 out of 5 average rating, 52 reviews
Top guest favourite
Flat in Winchester
The Carriage Inn - 1-bdrm apt in historic downtown
1 bedroom, 1 queen bed, 1 bathroom
20–25 Aug
4.93 out of 5 average rating, 122 reviews
Superhost
Flat in Winchester
RiverView 1 - Enjoy the view.
1 bedroom, 3 beds, 1 bathroom
21–26 Aug
4.8 out of 5 average rating, 69 reviews
Guest favourite
Home in Winchester
Bloomfield Garden House
2 bedrooms, 2 beds, 2 bathrooms
26–31 Aug
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Home in Winchester
Right Angle Country*Remote*Hot Tub~NO Cleaning FEE
2 bedrooms, 4 beds, 2 bathrooms
20–25 Aug
4.99 out of 5 average rating, 93 reviews
Top guest favourite
Farm stay in Winchester
LenMar Farm Country Stay near Lexington KY
2 bedrooms, 3 beds, 1 bathroom
14–19 Sept
4.94 out of 5 average rating, 193 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
Top guest favourite
Home in Richmond
Near to EKU and just minutes from I-75
1 bedroom, 1 bed, 1 bathroom
24–29 Aug
4.97 out of 5 average rating, 191 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, 145 reviews
Guest favourite
Home in Mount Sterling
Bourbon on the Hill
1 bedroom, 1 bed, 1 bathroom
20–25 Aug
4.97 out of 5 average rating, 38 reviews
Guest favourite
Home in Winchester
Comfortable Bluegrass Living
2 bedrooms, 3 beds, 1.5 bathrooms
1–6 Nov
5.0 out of 5 average rating, 17 reviews
Home in Winchester
Timeless Southern Elegance!
4 bedrooms, 5 beds, 4 bathrooms
20–25 Aug
New place to stay
Top guest favourite
Flat in Richmond
Westfield Green
2 bedrooms, 2 king beds, 1 bathroom
23–28 Aug
4.98 out of 5 average rating, 62 reviews
Tent in Richmond
The Highland Experience
1 bedroom, 1 bed, 1 bathroom
22–27 Aug
4.92 out of 5 average rating, 25 reviews
Top guest favourite
Room in Lexington
Lexington Home for Bluegrass Adventures
2 beds, 1 bathroom
6–11 Sept
4.96 out of 5 average rating, 885 reviews
Guest favourite
Flat in Mount Sterling
Pawplex
1 bedroom, 1 queen bed, 1 bathroom
30 Aug – 4 Sept
4.97 out of 5 average rating, 31 reviews