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Search results; Over 1,000 homes in Winchester

Descriptions are based on details hosts provide
Guest favourite
Cabin in Winchester
Historic Cabin - Farm - Near RRG, Lex, local music
2 bedrooms, 3 beds, 2 private bathrooms
19–24 Jul
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4.92 out of 5 average rating, 89 reviews
Guest favourite
Loft in Winchester
New York-style loft, historic renovation downtown
2 bedrooms, 2 beds, 2 bathrooms
15–20 Jul
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, 947 reviews
Guest favourite
Guest house in Winchester
Carriage house with a park view
1 bedroom, 1 queen bed, 1 bathroom
15–20 Jul
4.92 out of 5 average rating, 226 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
Restored 1890s loft above Italian restaurant
2 bedrooms, 2 king beds, 2 bathrooms
16–21 Jul
5.0 out of 5 average rating, 50 reviews
Top guest favourite
Farm stay in Winchester
10-acre Bluegrass farm with a fire pit
2 bedrooms, 3 beds, 1 bathroom
14–19 Sept
4.94 out of 5 average rating, 190 reviews
Top guest favourite
Flat in Winchester
Former carriage shop with courthouse views
1 bedroom, 1 queen bed, 1 bathroom
15–20 Jul
4.93 out of 5 average rating, 121 reviews
Top guest favourite
Farm stay in Winchester
Family Farm Winchester/Lexington 20 min.*Game Room
4 bedrooms, 8 beds, 3 bathrooms
19–24 Jul
4.97 out of 5 average rating, 142 reviews
Guest favourite
Home in Winchester
Comfortable Bluegrass Living
2 bedrooms, 3 beds, 1.5 bathrooms
27 Jul – 1 Aug
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Home in Winchester
Secluded homestead with a hot tub
2 bedrooms, 4 beds, 2 bathrooms
15–20 Jul
4.99 out of 5 average rating, 89 reviews
Top guest favourite
Farm stay in Winchester
*2Rm Farm Cottage*King Bed*5min DT Winchester
1 bedroom, 2 beds, 1 bathroom
19–24 Jul
5.0 out of 5 average rating, 94 reviews
Top guest favourite
Home in Winchester
Peacock Ranch House - Lexington and Winchester
3 bedrooms, 3 queen beds, 3.5 bathrooms
15–20 Jul
5.0 out of 5 average rating, 33 reviews
Superhost
Flat in Winchester
Industrial riverfront with a private deck
1 bedroom, 3 beds, 1 bathroom
16–21 Aug
4.79 out of 5 average rating, 67 reviews
Guest favourite
Cabin in Richmond
Secluded cabin on the KY River close to Lexington
3 bedrooms, 3 beds, 2 bathrooms
23–28 Jul
4.94 out of 5 average rating, 34 reviews
Top guest favourite
Home in Lexington
Lovely 3 Bdrm Home w/Free Parking Close to I-75
3 bedrooms, 5 beds, 2 bathrooms
18–23 Jul
4.92 out of 5 average rating, 144 reviews
Guest favourite
Home in Lexington
Private backyard with a playground and BBQ
4 bedrooms, 4 beds, 2.5 bathrooms
15–20 Jul
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in Waco
Game room, fire pit, and 2 ponds
5 bedrooms, 9 beds, 3 bathrooms
26–31 Jul
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Richmond
College-town Comfort
3 bedrooms, 4 beds, 1 bathroom
15–20 Jul
4.9 out of 5 average rating, 123 reviews