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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
19–24 Aug
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4.94 out of 5 average rating, 193 reviews
Guest favourite
Loft in Winchester
Stylish Loft 2Bdrm Winchester ky near Lexington
2 bedrooms, 2 beds
11–16 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
11–16 Aug
5.0 out of 5 average rating, 52 reviews
Guest favourite
Guest house in Winchester
Carriage House on the Park
1 bedroom, 1 queen bed
12–17 Aug
4.92 out of 5 average rating, 228 reviews
Top guest favourite
Home in Winchester
Right Angle Country*Remote*Hot Tub~NO Cleaning FEE
2 bedrooms, 4 beds
16–21 Aug
4.99 out of 5 average rating, 92 reviews
Guest favourite
Home in Winchester
Bloomfield Garden House
2 bedrooms, 2 beds
12–17 Aug
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in Winchester
Cozy Cottage
1 bedroom, 1 queen bed
13–18 Sept
4.92 out of 5 average rating, 956 reviews
Top guest favourite
Flat in Winchester
The Carriage Inn - 1-bdrm apt in historic downtown
1 bedroom, 1 queen bed
11–16 Aug
4.93 out of 5 average rating, 121 reviews
Guest favourite
Home in Winchester
Comfortable Bluegrass Living
2 bedrooms, 3 beds
12–17 Aug
5.0 out of 5 average rating, 17 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, 145 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 Lexington
The Coffee House
3 bedrooms, 3 beds
16–21 Aug
5.0 out of 5 average rating, 78 reviews
Guest favourite
Townhouse in Lexington
Bounce to Hamburg/I-75/St. Joe E
2 bedrooms, 2 beds
12–17 Aug
4.94 out of 5 average rating, 83 reviews
Guest favourite
Flat in Mount Sterling
Pawplex
1 bedroom, 1 queen bed
16–21 Aug
4.96 out of 5 average rating, 28 reviews
Guest favourite
Home in Clay City
Hidden Hideaway
2 bedrooms, 2 beds
17–22 Aug
4.88 out of 5 average rating, 8 reviews
Top guest favourite
Home in Richmond
College-town Comfort
3 bedrooms, 4 beds
12–17 Aug
4.9 out of 5 average rating, 124 reviews
Top guest favourite
Home in Ravenna
The River House
2 bedrooms, 2 beds
16–21 Aug
5.0 out of 5 average rating, 21 reviews
Guest favourite
Home in Mount Sterling
Bourbon on the Hill
1 bedroom, 1 bed
11–16 Aug
4.97 out of 5 average rating, 37 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, 98 reviews