Over 1,000 places in Winchester

Guest favorite
Guesthouse in Winchester
Carriage House on the Park
1 queen bed
Apr 1 – 6
4.95 out of 5 average rating, 155 reviews
Guest favorite
Loft in Winchester
Stylish Loft Historic Downtown 2Bdrm Winchester KY
2 beds
Apr 1 – 6
4.98 out of 5 average rating, 56 reviews
Home in Winchester
The Winchester 2
5 beds
Apr 1 – 6
5.0 out of 5 average rating, 4 reviews
Guest favorite
Home in Winchester
Cute 2 Story Home in Winchester
4 beds
Jun 4 – 9
5.0 out of 5 average rating, 12 reviews
Guest favorite
Farm stay in Winchester
Family Farm Winchester/Lexington 20 min.*Game Room
8 beds
Apr 13 – 18
4.96 out of 5 average rating, 83 reviews
Guest favorite
Apartment in Winchester
The Carriage Inn - 1-bdrm apt in historic downtown
1 queen bed
Apr 15 – 20
4.93 out of 5 average rating, 72 reviews
Guest favorite
Guesthouse in Winchester
Escape and unwind in the country
2 beds
Apr 29 – May 4
4.98 out of 5 average rating, 171 reviews
Home in Winchester
The Right Angle
4 beds
Apr 1 – 6
5.0 out of 5 average rating, 6 reviews
Guest favorite
Apartment in Winchester
The River House Floor 2 Getaway, w/a river view.
1 king bed
Apr 14 – 19
4.93 out of 5 average rating, 96 reviews
Guest favorite
Farm stay in Winchester
LenMar Farm Country Stay near Lexington KY
3 beds
Jun 4 – 9
4.93 out of 5 average rating, 101 reviews
Home in Winchester
Wi-Fi - Office Space - Full Gym Access - Park View
Apr 1 – 6
New place to stay
Guest favorite
Farm stay in Winchester
*Comfy King*2Rm Farm Cottage* DT Winchester 5 min.
2 beds
Apr 13 – 18
5.0 out of 5 average rating, 51 reviews
Guest favorite
Farm stay in Winchester
Renovated historic home on working cattle farm
2 beds
Apr 28 – May 3
4.88 out of 5 average rating, 41 reviews
Superhost
Home in Winchester
River Relaxation -3king beds
3 beds
Apr 6 – 11
4.86 out of 5 average rating, 35 reviews
Guest favorite
Loft in Winchester
Artist’s Loft 2Bdr Winchester, near Lexington KY
2 king beds
Jun 9 – 14
5.0 out of 5 average rating, 24 reviews
Guest favorite
Cottage in Winchester
Life is Better On The River (Hot Tub with a View)
3 beds
Apr 14 – 19
4.95 out of 5 average rating, 61 reviews
Guest favorite
Home in Winchester
Peacock Ranch House - Lexington and Winchester
3 queen beds
Apr 16 – 21
5.0 out of 5 average rating, 22 reviews
Guest favorite
Cabin in Mount Sterling
The Honey Hut, Think of “ On Golden Pond"
2 beds
Apr 6 – 11
4.95 out of 5 average rating, 199 reviews