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Search results; Over 1,000 homes in Winchester

Top guest favourite
Farm stay in Winchester
LenMar Farm Country Stay near Lexington KY
2 bedrooms, 3 beds, 1 private bathroom
17–22 Nov
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4.94 out of 5 average rating, 195 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
Stylish Loft 2Bdrm Winchester ky near Lexington
2 bedrooms, 2 beds, 2 bathrooms
13–18 Sept
4.96 out of 5 average rating, 104 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
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
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
*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
23–28 Sept
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
Guest favourite
Cabin in Lexington
1800’s Historical Log Cabin Lexington KY
2 bedrooms, 5 beds, 2.5 bathrooms
7–12 Nov
4.88 out of 5 average rating, 145 reviews
Guest favourite
Home in Richmond
Blue Skies Farm - King Suite - Beautiful Views
4 bedrooms, 6 beds, 3 bathrooms
12–17 Sept
4.86 out of 5 average rating, 28 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
Guest favourite
Home in Clay City
Hidden Hideaway
2 bedrooms, 2 beds, 1 bathroom
23–28 Sept
4.9 out of 5 average rating, 10 reviews
Top guest favourite
Flat in Mount Sterling
Historic 2-Bedroom Apartment in Downtown
2 bedrooms, 2 beds, 1 bathroom
12–17 Sept
4.97 out of 5 average rating, 92 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, 95 reviews
Top guest favourite
Flat in Richmond
Westfield Green
2 bedrooms, 2 king beds, 1 bathroom
13–18 Sept
4.99 out of 5 average rating, 69 reviews
Guest favourite
Home in Richmond
Silo Mill
1 bedroom, 1 bed, 1 bathroom
11–16 Sept
4.94 out of 5 average rating, 66 reviews
Top guest favourite
Barn in Richmond
The Barn-dominium
2 bedrooms, 2 queen beds, 1.5 bathrooms
13–18 Sept
4.95 out of 5 average rating, 237 reviews