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Search results; Over 1,000 homes in Winchester

Guest favorite
Guesthouse in Winchester
Carriage House on the Park
1 bedroom, 1 bed, 1 shared bath
Aug 13 – 18
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4.92 out of 5 average rating, 228 reviews
Guest favorite
Loft in Winchester
Stylish Loft 2Bdrm Winchester ky near Lexington
2 bedrooms, 2 beds, 2 baths
Aug 13 – 18
4.96 out of 5 average rating, 102 reviews
Guest favorite
Loft in Winchester
Artist’s Loft 2Bdr Winchester ky near Lexington
2 bedrooms, 2 king beds, 2 baths
Aug 13 – 18
5.0 out of 5 average rating, 52 reviews
Guest favorite
Home in Winchester
Bloomfield Garden House
2 bedrooms, 2 beds, 2 baths
Aug 13 – 18
5.0 out of 5 average rating, 10 reviews
Top guest favorite
Home in Winchester
Cozy Cottage
1 bedroom, 1 queen bed, 1 bath
Sep 13 – 18
4.92 out of 5 average rating, 957 reviews
Top guest favorite
Apartment in Winchester
The Carriage Inn - 1-bdrm apt in historic downtown
1 bedroom, 1 queen bed, 1 bath
Aug 13 – 18
4.93 out of 5 average rating, 121 reviews
Top guest favorite
Farm stay in Winchester
LenMar Farm Country Stay near Lexington KY
2 bedrooms, 3 beds, 1 bath
Aug 19 – 24
4.94 out of 5 average rating, 193 reviews
Top guest favorite
Home in Winchester
Right Angle Country*Remote*Hot Tub~NO Cleaning FEE
2 bedrooms, 4 beds, 2 baths
Aug 16 – 21
4.99 out of 5 average rating, 92 reviews
Guest favorite
Home in Winchester
Comfortable Bluegrass Living
2 bedrooms, 3 beds, 1.5 baths
Aug 13 – 18
5.0 out of 5 average rating, 17 reviews
Top guest favorite
Farm stay in Winchester
Family Farm Winchester/Lexington 20 min.*Game Room
4 bedrooms, 8 beds, 3 baths
Aug 30 – Sep 4
4.97 out of 5 average rating, 145 reviews
Superhost
Apartment in Winchester
RiverView 1 - Enjoy the view.
1 bedroom, 3 beds, 1 bath
Aug 16 – 21
4.79 out of 5 average rating, 68 reviews
Guest favorite
Cabin in Winchester
Historic Cabin - Farm - Near RRG, Lex, local music
2 bedrooms, 3 beds, 2 baths
Aug 16 – 21
4.92 out of 5 average rating, 91 reviews
Top guest favorite
Loft in Mount Sterling
One Bedroom apartment with full kitchen
1 bedroom, 1 king bed, 1 bath
Jan 4 – 9
4.98 out of 5 average rating, 64 reviews
Guest favorite
Apartment in Mount Sterling
Pawplex
1 bedroom, 1 queen bed, 1 bath
Aug 30 – Sep 4
4.96 out of 5 average rating, 28 reviews
Top guest favorite
Farm stay in Winchester
*2Rm Farm Cottage*King Bed*5min DT Winchester
1 bedroom, 2 beds, 1 bath
Aug 30 – Sep 4
5.0 out of 5 average rating, 98 reviews
Top guest favorite
Cabin in Nicholasville
The Lodge at Marble Creek
3 bedrooms, 4 beds, 2 baths
Sep 13 – 18
4.98 out of 5 average rating, 49 reviews
Guest favorite
Townhouse in Lexington
Bounce to Hamburg/I-75/St. Joe E
2 bedrooms, 2 beds, 2.5 baths
Aug 21 – 26
4.94 out of 5 average rating, 83 reviews
Top guest favorite
Home in Mount Sterling
High Street Hideaway home atmosphere for relaxing
2 bedrooms, 2 queen beds, 2 baths
Aug 13 – 18
5.0 out of 5 average rating, 112 reviews
Top guest favorite
Home in Paris
Stoner View Farm
3 bedrooms, 4 beds, 1.5 baths
Aug 14 – 19
4.94 out of 5 average rating, 207 reviews