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Search results; Over 1,000 homes in Winchester

Guest favourite
Cottage in Winchester
Life is Better On The River
2 bedrooms, 3 beds, 2 private bathrooms
12–17 Oct
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4.88 out of 5 average rating, 137 reviews
Guest favourite
Loft in Winchester
Stylish Loft 2Bdrm Winchester ky near Lexington
2 bedrooms, 2 beds, 2 bathrooms
13–18 Sept
4.96 out of 5 average rating, 103 reviews
Top guest favourite
Home in Winchester
Cozy Cottage
1 bedroom, 1 queen bed, 1 bathroom
2–7 Nov
4.92 out of 5 average rating, 965 reviews
Guest favourite
Loft in Winchester
Artist’s Loft 2Bdr Winchester ky near Lexington
2 bedrooms, 2 king beds, 2 bathrooms
21–26 Sept
5.0 out of 5 average rating, 52 reviews
Top guest favourite
Farm stay in Winchester
Family Farm Winchester/Lexington 20 min.*Game Room
4 bedrooms, 8 beds, 3 bathrooms
16–21 Sept
4.97 out of 5 average rating, 145 reviews
Top guest favourite
Farm stay in Winchester
LenMar Farm Country Stay near Lexington KY
2 bedrooms, 3 beds, 1 bathroom
17–22 Nov
4.94 out of 5 average rating, 195 reviews
Top guest favourite
Flat in Winchester
The Carriage Inn - 1-bdrm apt in historic downtown
1 bedroom, 1 queen bed, 1 bathroom
23–28 Sept
4.93 out of 5 average rating, 123 reviews
Guest favourite
Guest house in Winchester
Carriage House on the Park
1 bedroom, 1 queen bed, 1 bathroom
30 Sept – 5 Oct
4.92 out of 5 average rating, 229 reviews
Top guest favourite
Farm stay in Winchester
*2Rm Farm Cottage*King Bed*5min DT Winchester
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 98 reviews
Guest favourite
Home in Winchester
Bloomfield Garden House
2 bedrooms, 2 beds, 2 bathrooms
26–31 May
5.0 out of 5 average rating, 12 reviews
Guest favourite
Flat in Winchester
RiverView 1 - Enjoy the view.
1 bedroom, 3 beds, 1 bathroom
20–25 Sept
4.8 out of 5 average rating, 70 reviews
Top guest favourite
Home in Winchester
Right Angle Country*Remote*Hot Tub~NO Cleaning FEE
2 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.99 out of 5 average rating, 94 reviews
Guest favourite
Cabin in Winchester
Historic Cabin - Farm - Near RRG, Lex, local music
2 bedrooms, 3 beds, 2 bathrooms
9–14 Sept
4.92 out of 5 average rating, 91 reviews
Top guest favourite
Home in Winchester
Peacock Ranch House - Lexington and Winchester
3 bedrooms, 3 queen beds, 3.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 34 reviews
Guest favourite
Home in Lexington
Country cottage in the heart of the Bluegrass
3 bedrooms, 3 beds, 1 bathroom
28 Sept – 3 Oct
4.93 out of 5 average rating, 30 reviews
Top guest favourite
Home in Clay City
Mountain Retreat | Pool, Pond, Views & Wi-Fi
3 bedrooms, 5 beds, 1 bathroom
19–24 Sept
4.88 out of 5 average rating, 25 reviews
Top guest favourite
Guest house in Lexington
Conveniently located to UK, Keeneland and Hamburg
3 bedrooms, 6 beds, 2 bathrooms
17–22 Dec
4.97 out of 5 average rating, 98 reviews
Guest favourite
Home in Winchester
Comfortable Bluegrass Living
2 bedrooms, 3 beds, 1.5 bathrooms
1–6 Nov
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Home in Richmond
Newly Built Town & Country
3 bedrooms, 3 beds, 2.5 bathrooms
13–18 Sept
4.99 out of 5 average rating, 141 reviews