Search results; Over 1,000 homes

Place to stay in Winchester
Oasis at the Halls
10-min drive
14–19 Jul
New place to stay
Top guest favourite
Guest house in Winchester
Carriage House Gardenside
10-min drive
28 Jul – 2 Aug
4.96 out of 5 average rating, 120 reviews
Top guest favourite
Home in Winchester
Cozy Cottage
10-min drive
13–18 Sept
4.92 out of 5 average rating, 947 reviews
Guest favourite
Loft in Winchester
Stylish Loft 2Bdrm Winchester ky near Lexington
10-min drive
14–19 Jul
4.96 out of 5 average rating, 100 reviews
Guest favourite
Loft in Winchester
Artist’s Loft 2Bdr Winchester ky near Lexington
10-min drive
16–21 Jul
5.0 out of 5 average rating, 50 reviews
Guest favourite
Home in Winchester
Bloomfield Garden House
10-min drive
11–16 Aug
5.0 out of 5 average rating, 7 reviews
Superhost
Home in Winchester
The Winchester
10-min drive
16–21 Aug
4.81 out of 5 average rating, 53 reviews
Top guest favourite
Flat in Winchester
The Carriage Inn - 1-bdrm apt in historic downtown
10-min drive
14–19 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
20-min drive
19–24 Jul
4.97 out of 5 average rating, 142 reviews
Superhost
Home in Winchester
Birdie’s House
10-min drive
2–7 Aug
4.76 out of 5 average rating, 42 reviews
Guest favourite
Home in Winchester
Comfortable Bluegrass Living
10-min drive
27 Jul – 1 Aug
5.0 out of 5 average rating, 13 reviews
Guest favourite
Cottage in Winchester
Life is Better On The River
20-min drive
31 Aug – 5 Sept
4.89 out of 5 average rating, 131 reviews
Superhost
Home in Nicholasville
The Lodge A-Frame Getaway
1 bed
18–23 Jul
4.92 out of 5 average rating, 12 reviews
Top guest favourite
Home in Lexington
The Flower Pot
40-min drive
27 Jul – 1 Aug
4.99 out of 5 average rating, 171 reviews
Guest favourite
Home in Lexington
Hot Tub/Firepit/King Beds/Fenced Yard/Playground
40-min drive
30 Aug – 4 Sept
5.0 out of 5 average rating, 22 reviews
Guest favourite
Home in Lexington
Home Away From Home
30-min drive
14–19 Jul
5.0 out of 5 average rating, 10 reviews
Guest favourite
Townhouse in Lexington
Bounce to Hamburg/I-75/St. Joe E
30-min drive
19–24 Jul
4.94 out of 5 average rating, 80 reviews
Superhost
Flat in Winchester
RiverView 1 - Enjoy the view.
20-min drive
16–21 Aug
4.79 out of 5 average rating, 67 reviews