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Search results; Over 1,000 homes in Winchester

Guest favourite
Home in Winchester
Cozy Cottage
1 bedroom, 1 bed, 1 private bathroom
13–18 Sept
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4.92 out of 5 average rating, 956 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, 101 reviews
Guest favourite
Loft in Winchester
Artist’s Loft 2Bdr Winchester ky near Lexington
2 bedrooms, 2 king beds
9–14 Aug
5.0 out of 5 average rating, 52 reviews
Top guest favourite
Home in Winchester
Right Angle Country*Remote*Hot Tub~NO Cleaning FEE
2 bedrooms, 4 beds
9–14 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
Top guest favourite
Flat in Winchester
The Carriage Inn - 1-bdrm apt in historic downtown
1 bedroom, 1 queen bed
9–14 Aug
4.93 out of 5 average rating, 121 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
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, 193 reviews
Guest favourite
Home in Winchester
Comfortable Bluegrass Living
2 bedrooms, 3 beds
10–15 Aug
5.0 out of 5 average rating, 16 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
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
Guest favourite
Flat in Mount Sterling
Pawplex
1 bedroom, 1 queen bed
16–21 Aug
4.96 out of 5 average rating, 26 reviews
Top guest favourite
Home in Lexington
The Coffee House
3 bedrooms, 3 beds
16–21 Aug
5.0 out of 5 average rating, 77 reviews
Top guest favourite
Cabin in Nicholasville
The Lodge at Marble Creek
3 bedrooms, 4 beds
13–18 Sept
4.98 out of 5 average rating, 48 reviews
Guest favourite
Home in Clay City
Hidden Hideaway
2 bedrooms, 2 beds
17–22 Aug
4.83 out of 5 average rating, 6 reviews
Top guest favourite
Cabin in Waco
Stunning Cedar Cabin, Hot Tub, Amazing Views!
1 bedroom, 1 king bed
10–15 Aug
4.98 out of 5 average rating, 145 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
Guest favourite
Home in Mount Sterling
Bourbon on the Hill
1 bedroom, 1 bed
9–14 Aug
4.97 out of 5 average rating, 37 reviews
Guest favourite
Home in Lexington
Relaxing Retreat w/ Fenced Yard & Patio
3 bedrooms, 4 beds
9–14 Aug
5.0 out of 5 average rating, 11 reviews