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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, 90 reviews
Guest favourite
Loft in Winchester
Stylish Loft 2Bdrm Winchester ky near Lexington
2 bedrooms, 2 beds
19–24 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
19–24 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, 949 reviews
Top guest favourite
Home in Winchester
Right Angle Country*Remote*Hot Tub~NO Cleaning FEE
2 bedrooms, 4 beds
19–24 Jul
4.99 out of 5 average rating, 89 reviews
Top guest favourite
Flat in Winchester
The Carriage Inn - 1-bdrm apt in historic downtown
1 bedroom, 1 queen bed
19–24 Jul
4.93 out of 5 average rating, 121 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
Family Farm Winchester/Lexington 20 min.*Game Room
4 bedrooms, 8 beds
19–24 Jul
4.97 out of 5 average rating, 143 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, 121 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
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, 95 reviews
Guest favourite
Home in Mount Sterling
Bourbon on the Hill
1 bedroom, 1 bed
19–24 Jul
4.97 out of 5 average rating, 34 reviews
Guest favourite
Home in Winchester
Comfortable Bluegrass Living
2 bedrooms, 3 beds
4–9 Aug
5.0 out of 5 average rating, 13 reviews
Guest favourite
Home in Lexington
The Coffee House
3 bedrooms, 3 beds
26–31 Jul
5.0 out of 5 average rating, 71 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, 44 reviews
Superhost
Cabin in Winston
Social Distance/127 Private Acres -Hot Tub -Wi-Fi
2 bedrooms, 2 double beds
27 Jul – 1 Aug
New place to stay
Superhost
Flat in Winchester
RiverView 1 - Enjoy the view.
1 bedroom, 3 beds
26–31 Jul
4.79 out of 5 average rating, 67 reviews
Top guest favourite
Home in Irvine
Pauline's Paradise
2 bedrooms, 3 beds
3–8 Aug
4.99 out of 5 average rating, 137 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