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Search results; Over 1,000 homes in Winchester

Guest favourite
Loft in Winchester
Stylish Loft 2Bdrm Winchester ky near Lexington
2 bedrooms, 2 beds, 2 private bathrooms
21–26 Jul
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4.96 out of 5 average rating, 100 reviews
Top guest favourite
Home in Winchester
Cozy Cottage
1 bedroom, 1 queen bed, 1 bathroom
13–18 Sept
4.92 out of 5 average rating, 950 reviews
Top guest favourite
Guest house in Winchester
Carriage House Gardenside
1 bedroom, 1 king bed, 1 bathroom
28 Jul – 2 Aug
4.96 out of 5 average rating, 121 reviews
Top guest favourite
Flat in Winchester
The Carriage Inn - 1-bdrm apt in historic downtown
1 bedroom, 1 queen bed, 1 bathroom
21–26 Jul
4.93 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, 1 bathroom
14–19 Sept
4.94 out of 5 average rating, 190 reviews
Guest favourite
Home in Winchester
Bloomfield Garden House
2 bedrooms, 2 beds, 2 bathrooms
11–16 Aug
5.0 out of 5 average rating, 7 reviews
Guest favourite
Loft in Winchester
Artist’s Loft 2Bdr Winchester ky near Lexington
2 bedrooms, 2 king beds, 2 bathrooms
21–26 Jul
5.0 out of 5 average rating, 50 reviews
Top guest favourite
Farm stay in Winchester
*2Rm Farm Cottage*King Bed*5min DT Winchester
1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 95 reviews
Top guest favourite
Home in Winchester
Right Angle Country*Remote*Hot Tub~NO Cleaning FEE
2 bedrooms, 4 beds, 2 bathrooms
21–26 Jul
4.99 out of 5 average rating, 89 reviews
Guest favourite
Home in Winchester
Comfortable Bluegrass Living
2 bedrooms, 3 beds, 1.5 bathrooms
4–9 Aug
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Home in Mount Sterling
High Street Hideaway home atmosphere for relaxing
2 bedrooms, 2 queen beds, 2 bathrooms
21–26 Jul
5.0 out of 5 average rating, 111 reviews
Superhost
Flat in Winchester
RiverView 1 - Enjoy the view.
1 bedroom, 3 beds, 1 bathroom
16–21 Aug
4.79 out of 5 average rating, 67 reviews
Guest favourite
Farm stay in Mount Sterling
Mount Sterling Horse Farm
4 bedrooms, 4 beds, 2.5 bathrooms
21–26 Jul
4.97 out of 5 average rating, 30 reviews
Top guest favourite
Home in Richmond
Silo Mill
1 bedroom, 1 bed, 1 bathroom
3–8 Aug
4.96 out of 5 average rating, 49 reviews
Top guest favourite
Home in Sharpsburg
Peaceful Kentucky Ranch
3 bedrooms, 3 beds, 2.5 bathrooms
21–26 Jul
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Home in Paris
Stoner View Farm
3 bedrooms, 4 beds, 1.5 bathrooms
23–28 Jul
4.94 out of 5 average rating, 206 reviews
Guest favourite
Home in Lexington
The Coffee House
3 bedrooms, 3 beds, 2 bathrooms
24–29 Jul
5.0 out of 5 average rating, 71 reviews
Top guest favourite
Farm stay in Winchester
Family Farm Winchester/Lexington 20 min.*Game Room
4 bedrooms, 8 beds, 3 bathrooms
30 Aug – 4 Sept
4.97 out of 5 average rating, 144 reviews
Guest favourite
Flat in Lexington
Location! DWTN next to Rupp, KING BED w/ Parking
1 bedroom, 1 king bed, 1 bathroom
23–28 Aug
4.93 out of 5 average rating, 146 reviews