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Search results; Over 1,000 places

Guest favorite
Home in Winchester
Cozy Cottage
7 min drive
May 12 – 17
4.91 out of 5 average rating, 672 reviews
Guest favorite
Farm stay in Winchester
Family Farm Winchester/Lexington 20 min.*Game Room
10 min drive
May 6 – 11
4.97 out of 5 average rating, 87 reviews
Guest favorite
Home in Winchester
Cute 2 Story Home in Winchester
4 min drive
May 13 – 18
5.0 out of 5 average rating, 13 reviews
Superhost
Home in Winchester
The Winchester 2
4 min drive
May 5 – 10
5.0 out of 5 average rating, 4 reviews
Guest favorite
Farm stay in Winchester
Renovated historic home on working cattle farm
10 min drive
Apr 28 – May 3
4.88 out of 5 average rating, 42 reviews
Guest favorite
Loft in Winchester
Stylish Loft Historic Downtown 2Bdrm Winchester KY
5 min drive
Apr 28 – May 3
4.98 out of 5 average rating, 57 reviews
Guest favorite
Farm stay in Winchester
LenMar Farm Country Stay near Lexington KY
13 min drive
Jun 18 – 23
4.93 out of 5 average rating, 106 reviews
Guest favorite
Apartment in Winchester
The Carriage Inn - 1-bdrm apt in historic downtown
5 min drive
Apr 20 – 25
4.93 out of 5 average rating, 73 reviews
Guest favorite
Home in Winchester
NEW Serene Country Refuge at The Right Angle
27 min drive
Apr 20 – 25
5.0 out of 5 average rating, 13 reviews
Guest favorite
Guesthouse in Winchester
Carriage House on the Park
5 min drive
May 22 – 27
4.95 out of 5 average rating, 159 reviews
Guest favorite
Farm stay in Winchester
2Rm*Farm Cottage*Comfy King * DT Winchester 5 min.
10 min drive
Apr 21 – 26
5.0 out of 5 average rating, 54 reviews
Guest favorite
Barn in Lexington
Stay with our horses and goats on a private farm
22 min drive
Jun 9 – 14
4.93 out of 5 average rating, 292 reviews
Superhost
Home in Winchester
River Relaxation -3king beds
14 min drive
May 18 – 23
4.82 out of 5 average rating, 39 reviews
Guest favorite
Guesthouse in Winchester
Escape and unwind in the country
28 min drive
May 6 – 11
4.98 out of 5 average rating, 174 reviews
Guest favorite
Home in Winchester
Peacock Ranch House - Lexington and Winchester
9 min drive
Apr 20 – 25
5.0 out of 5 average rating, 22 reviews
Guest favorite
Cabin in Mount Sterling
The Honey Hut, Think of “ On Golden Pond"
35 min drive
Apr 21 – 26
4.96 out of 5 average rating, 202 reviews
Guest favorite
Treehouse in Georgetown
Treehouse with TWO outdoor tubs by the creek!
39 min drive
Apr 28 – May 3
4.98 out of 5 average rating, 86 reviews
Guest favorite
Cabin in Richmond
Private cabin on KY River/Hot tub/30 miles to Lex
39 min drive
May 12 – 17
4.96 out of 5 average rating, 50 reviews