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Search results; Over 1,000 homes in Winchester

Guest favourite
Loft in Winchester
Stylish Loft 2Bdrm Winchester ky near Lexington
2 bedrooms, 2 beds, 2 private bathrooms
14–19 Jul
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4.96 out of 5 average rating, 99 reviews
Top guest favourite
Farm stay in Winchester
LenMar Farm Country Stay near Lexington KY
2 bedrooms, 3 beds
13–18 Jul
4.94 out of 5 average rating, 189 reviews
Top guest favourite
Home in Winchester
Cozy Cottage
1 bedroom, 1 queen bed
13–18 Sept
4.92 out of 5 average rating, 945 reviews
Guest favourite
Loft in Winchester
Artist’s Loft 2Bdr Winchester ky near Lexington
2 bedrooms, 2 king beds
12–17 Jul
5.0 out of 5 average rating, 50 reviews
Guest favourite
Home in Winchester
Bloomfield Garden House
2 bedrooms, 2 beds
11–16 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Flat in Winchester
The Carriage Inn - 1-bdrm apt in historic downtown
1 bedroom, 1 queen bed
7–12 Jul
4.93 out of 5 average rating, 121 reviews
Top guest favourite
Guest house in Winchester
Carriage House Gardenside
1 bedroom, 1 king bed
28 Jul – 2 Aug
4.96 out of 5 average rating, 120 reviews
Guest favourite
Home in Winchester
Comfortable Bluegrass Living
2 bedrooms, 3 beds
27 Jul – 1 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Farm stay in Winchester
Family Farm Winchester/Lexington 20 min.*Game Room
4 bedrooms, 8 beds
19–24 Jul
4.97 out of 5 average rating, 142 reviews
Guest favourite
Farm stay in Winchester
The Winchester Retreat
1 bedroom, 1 bed
16–21 May
4.83 out of 5 average rating, 157 reviews
Top guest favourite
Home in Winchester
Country Refuge @ The Right Angle *Remote *Hot Tub
2 bedrooms, 4 beds
7–12 Jul
4.99 out of 5 average rating, 89 reviews
Guest favourite
Cabin in Winchester
Historic Cabin - Farm - Near RRG, Lex, local music
2 bedrooms, 3 beds
19–24 Jul
4.92 out of 5 average rating, 89 reviews
Top guest favourite
Home in Winchester
Peacock Ranch House - Lexington and Winchester
3 bedrooms, 3 queen beds
7–12 Jul
5.0 out of 5 average rating, 33 reviews
Guest favourite
Flat in Winchester
RiverView 1 - Enjoy the view.
1 bedroom, 3 beds
12–17 Jul
4.79 out of 5 average rating, 67 reviews
Top guest favourite
Farm stay in Winchester
*2Rm Farm Cottage*King Bed*5min DT Winchester
1 bedroom, 2 beds
19–24 Jul
5.0 out of 5 average rating, 94 reviews
Top guest favourite
Home in Lexington
Lovely 3 Bdrm Home w/Free Parking Close to I-75
3 bedrooms, 5 beds
2–7 Aug
4.92 out of 5 average rating, 144 reviews
Top guest favourite
Farm stay in Paris
Welcome Hall - Classic & Beautiful Horse Farm Stay
5 bedrooms, 7 beds
12–17 Aug
4.98 out of 5 average rating, 119 reviews
Top guest favourite
Home in Lexington
Home Away From Home
4 bedrooms, 4 beds
12–17 Jul
5.0 out of 5 average rating, 10 reviews
Superhost
Flat in Mount Sterling
Pawplex
1 bedroom, 1 queen bed
18–23 Jul
4.95 out of 5 average rating, 19 reviews