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Search results; Over 1,000 homes in Winchester

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Top guest favourite
Home in Winchester
Right Angle Country*Remote*Hot Tub~NO Cleaning FEE
2 bedrooms, 4 beds, 2 private bathrooms
6–11 Sept
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4.99 out of 5 average rating, 93 reviews
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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
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Top guest favourite
Guest house in Winchester
Carriage House Gardenside
1 bedroom, 1 king bed, 1 bathroom
3–8 Sept
4.96 out of 5 average rating, 124 reviews
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Guest favourite
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
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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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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Top guest favourite
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
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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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
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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Guest favourite
Home in Winchester
Bloomfield Garden House
2 bedrooms, 2 beds, 2 bathrooms
26–31 May
5.0 out of 5 average rating, 11 reviews
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Home in Richmond
Blue Skies Farm - King Suite - Beautiful Views
4 bedrooms, 6 beds, 3 bathrooms
8–13 Sept
4.85 out of 5 average rating, 27 reviews
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Superhost
Home in Richmond
Walnut Creek Retreat - King Suit - Waterfall
3 bedrooms, 4 beds, 2.5 bathrooms
6–11 Sept
4.97 out of 5 average rating, 75 reviews
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Top guest favourite
Barn in Paris
Horse & Flower Farm Barn Loft
3 bedrooms, 3 beds, 1 bathroom
3–8 Sept
4.96 out of 5 average rating, 100 reviews
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Hotel room in Lexington
Hotel LEX | Courtyard 2 Queen | Indoor Pool
1 bedroom, 2 queen beds, 1 bathroom
1–6 Sept
New place to stay
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Top guest favourite
Cabin in Waco
Stunning Cedar Cabin, Hot Tub, Amazing Views!
1 bedroom, 1 king bed, 1.5 bathrooms
7–12 Sept
4.98 out of 5 average rating, 146 reviews
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Home in Richmond
Silo Mill
1 bedroom, 1 bed, 1 bathroom
11–16 Sept
4.95 out of 5 average rating, 62 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