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Search results; Over 1,000 homes in Winchester

Guest favourite
Cabin in Winchester
Historic Cabin - Farm - Near RRG, Lex, local music
2 bedrooms, 3 beds, 2 private bathrooms
19–24 Jul
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4.92 out of 5 average rating, 89 reviews
Guest favourite
Loft in Winchester
Stylish Loft 2Bdrm Winchester ky near Lexington
2 bedrooms, 2 beds
16–21 Jul
4.96 out of 5 average rating, 100 reviews
Guest favourite
Loft in Winchester
Artist’s Loft 2Bdr Winchester ky near Lexington
2 bedrooms, 2 king beds
16–21 Jul
5.0 out of 5 average rating, 50 reviews
Top guest favourite
Home in Winchester
Cozy Cottage
1 bedroom, 1 queen bed
13–18 Sept
4.92 out of 5 average rating, 948 reviews
Guest favourite
Guest house in Winchester
Carriage House on the Park
1 bedroom, 1 queen bed
16–21 Jul
4.92 out of 5 average rating, 226 reviews
Top guest favourite
Flat in Winchester
The Carriage Inn - 1-bdrm apt in historic downtown
1 bedroom, 1 queen bed
16–21 Jul
4.93 out of 5 average rating, 121 reviews
Top guest favourite
Home in Winchester
Right Angle Country*Remote*Hot Tub~NO Cleaning FEE
2 bedrooms, 4 beds
16–21 Jul
4.99 out of 5 average rating, 89 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
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, 190 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
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
Guest favourite
Home in Winchester
Comfortable Bluegrass Living
2 bedrooms, 3 beds
27 Jul – 1 Aug
5.0 out of 5 average rating, 13 reviews
Superhost
Flat in Winchester
RiverView 1 - Enjoy the view.
1 bedroom, 3 beds
23–28 Jul
4.79 out of 5 average rating, 67 reviews
Guest favourite
Home in Mount Sterling
Bourbon on the Hill
1 bedroom, 1 bed
18–23 Jul
4.97 out of 5 average rating, 34 reviews
Top guest favourite
Loft in Mount Sterling
One Bedroom apartment with full kitchen
1 bedroom, 1 king bed
4–9 Jan
4.98 out of 5 average rating, 64 reviews
Top guest favourite
Cabin in Mount Sterling
The Honey Hut, Think of “ On Golden Pond"
1 bedroom, 2 beds
9–14 Aug
4.97 out of 5 average rating, 296 reviews
Guest favourite
Home in Lexington
The Coffee House
3 bedrooms, 3 beds
26–31 Jul
5.0 out of 5 average rating, 69 reviews
Guest favourite
Townhouse in Lexington
Bounce to Hamburg/I-75/St. Joe E
2 bedrooms, 2 beds
19–24 Jul
4.94 out of 5 average rating, 80 reviews
Top guest favourite
Home in Winchester
Peacock Ranch House - Lexington and Winchester
3 bedrooms, 3 queen beds
16–21 Jul
5.0 out of 5 average rating, 33 reviews