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Search results; Over 1,000 homes in Winchester

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Top guest favourite
Guest house in Winchester
Carriage House Gardenside
1 bedroom, 1 bed, 1 private bathroom
3–8 Sept
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4.96 out of 5 average rating, 124 reviews
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Home in Winchester
Cozy Cottage
1 bedroom, 1 queen bed, 1 bathroom
2–7 Nov
4.92 out of 5 average rating, 964 reviews
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Loft in Winchester
Stylish Loft 2Bdrm Winchester ky near Lexington
2 bedrooms, 2 beds, 2 bathrooms
1–6 Sept
4.96 out of 5 average rating, 102 reviews
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Guest favourite
Guest house in Winchester
Carriage House on the Park
1 bedroom, 1 queen bed, 1 bathroom
2–7 Sept
4.92 out of 5 average rating, 229 reviews
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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
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Farm stay in Winchester
Family Farm Winchester/Lexington 20 min.*Game Room
4 bedrooms, 8 beds, 3 bathrooms
10–15 Sept
4.97 out of 5 average rating, 145 reviews
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Farm stay in Winchester
LenMar Farm Country Stay near Lexington KY
2 bedrooms, 3 beds, 1 bathroom
14–19 Sept
4.94 out of 5 average rating, 195 reviews
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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
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Cabin in Winchester
Historic Cabin - Farm - Near RRG, Lex, local music
2 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
4.92 out of 5 average rating, 91 reviews
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Flat in Winchester
RiverView 1 - Enjoy the view.
1 bedroom, 3 beds, 1 bathroom
13–18 Sept
4.8 out of 5 average rating, 70 reviews
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Top guest favourite
Farm stay in Winchester
*2Rm Farm Cottage*King Bed*5min DT Winchester
1 bedroom, 2 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 98 reviews
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Top guest favourite
Home in Winchester
Right Angle Country*Remote*Hot Tub~NO Cleaning FEE
2 bedrooms, 4 beds, 2 bathrooms
6–11 Sept
4.99 out of 5 average rating, 93 reviews
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Home in Winchester
Timeless Southern Elegance!
4 bedrooms, 5 beds, 4 bathrooms
1–6 Sept
New place to stay
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Home in Lexington
Country cottage in the heart of the Bluegrass
3 bedrooms, 3 beds, 1 bathroom
1–6 Sept
4.93 out of 5 average rating, 30 reviews
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Flat in Mount Sterling
Pawplex
1 bedroom, 1 queen bed, 1 bathroom
13–18 Sept
4.97 out of 5 average rating, 33 reviews
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Top guest favourite
Home in Winchester
Peacock Ranch House - Lexington and Winchester
3 bedrooms, 3 queen beds, 3.5 bathrooms
6–11 Sept
5.0 out of 5 average rating, 33 reviews
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Home in Lexington
The Coffee House
3 bedrooms, 3 beds, 2 bathrooms
6–11 Sept
5.0 out of 5 average rating, 84 reviews
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Home in Richmond
Newly Built Town & Country
3 bedrooms, 3 beds, 2.5 bathrooms
1–6 Sept
4.99 out of 5 average rating, 139 reviews
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Superhost
Home in Richmond
College-town Comfort
3 bedrooms, 4 beds, 1 bathroom
7–12 Sept
4.9 out of 5 average rating, 125 reviews