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Search results; Over 1,000 homes in Winchester
Over 1,000 homes in Winchester
Guest favorite
Guest favorite
Home in Winchester
Cozy Cottage
1 queen bed
1 queen bed
May 12 – 17
May 12 – 17
G$14,307 GYD
night
G$14,307 GYD per night
4.91 out of 5 average rating, 672 reviews
4.91 (672)
Apartment in Winchester
The Winchester Cozy One Bedroom!
1 queen bed
1 queen bed
Apr 30 – May 5
Apr 30 – May 5
G$13,929 GYD
night
G$13,929 GYD per night
4.7 out of 5 average rating, 20 reviews
4.7 (20)
Guest favorite
Guest favorite
Home in Winchester
NEW Serene Country Refuge at The Right Angle
4 beds
4 beds
Apr 20 – 25
Apr 20 – 25
G$32,134 GYD
G$23,621 GYD
night
G$23,621 GYD per night, originally G$32,134 GYD
5.0 out of 5 average rating, 13 reviews
5.0 (13)
Guest favorite
Guest favorite
Apartment in Winchester
The Carriage Inn - 1-bdrm apt in historic downtown
1 queen bed
1 queen bed
Apr 20 – 25
Apr 20 – 25
G$20,237 GYD
night
G$20,237 GYD per night
4.93 out of 5 average rating, 73 reviews
4.93 (73)
Guest favorite
Guest favorite
Guesthouse in Winchester
Escape and unwind in the country
2 beds
2 beds
May 6 – 11
May 6 – 11
G$20,269 GYD
night
G$20,269 GYD per night
4.98 out of 5 average rating, 174 reviews
4.98 (174)
Guest favorite
Guest favorite
Guesthouse in Winchester
Carriage House on the Park
1 queen bed
1 queen bed
May 22 – 27
May 22 – 27
G$19,653 GYD
night
G$19,653 GYD per night
4.95 out of 5 average rating, 159 reviews
4.95 (159)
Guest favorite
Guest favorite
Loft in Winchester
Stylish Loft Historic Downtown 2Bdrm Winchester KY
2 beds
2 beds
Apr 28 – May 3
Apr 28 – May 3
G$35,820 GYD
night
G$35,820 GYD per night
4.98 out of 5 average rating, 57 reviews
4.98 (57)
Guest favorite
Guest favorite
Home in Winchester
Cute 2 Story Home in Winchester
4 beds
4 beds
May 13 – 18
May 13 – 18
G$43,035 GYD
night
G$43,035 GYD per night
5.0 out of 5 average rating, 13 reviews
5.0 (13)
Guest favorite
Guest favorite
Farm stay in Winchester
LenMar Farm Country Stay near Lexington KY
3 beds
3 beds
Jun 18 – 23
Jun 18 – 23
G$26,564 GYD
night
G$26,564 GYD per night
4.93 out of 5 average rating, 106 reviews
4.93 (106)
Guest favorite
Guest favorite
Apartment in Winchester
The River House Floor 2 Getaway, w/a river view.
1 king bed
1 king bed
May 5 – 10
May 5 – 10
G$19,283 GYD
night
G$19,283 GYD per night
4.92 out of 5 average rating, 99 reviews
4.92 (99)
Superhost
Superhost
Farm stay in Winchester
The Winchester Retreat
1 bed
1 bed
May 9 – 14
May 9 – 14
G$27,995 GYD
G$23,607 GYD
night
G$23,607 GYD per night, originally G$27,995 GYD
4.86 out of 5 average rating, 43 reviews
4.86 (43)
Guest favorite
Guest favorite
Farm stay in Winchester
Renovated historic home on working cattle farm
2 beds
2 beds
Apr 28 – May 3
Apr 28 – May 3
G$31,203 GYD
night
G$31,203 GYD per night
4.88 out of 5 average rating, 42 reviews
4.88 (42)
Guest favorite
Guest favorite
Farm stay in Winchester
2Rm*Farm Cottage*Comfy King * DT Winchester 5 min.
2 beds
2 beds
Apr 21 – 26
Apr 21 – 26
G$22,264 GYD
G$18,573 GYD
night
G$18,573 GYD per night, originally G$22,264 GYD
5.0 out of 5 average rating, 54 reviews
5.0 (54)
Guest favorite
Guest favorite
Farm stay in Winchester
Family Farm Winchester/Lexington 20 min.*Game Room
8 beds
8 beds
May 6 – 11
May 6 – 11
G$60,173 GYD
G$50,653 GYD
night
G$50,653 GYD per night, originally G$60,173 GYD
4.97 out of 5 average rating, 87 reviews
4.97 (87)
Superhost
Superhost
Home in Winchester
River Relaxation -3king beds
3 beds
3 beds
May 18 – 23
May 18 – 23
G$43,301 GYD
night
G$43,301 GYD per night
4.82 out of 5 average rating, 39 reviews
4.82 (39)
Superhost
Superhost
Home in Winchester
The Winchester 2
5 beds
5 beds
May 5 – 10
May 5 – 10
G$47,101 GYD
G$38,743 GYD
night
G$38,743 GYD per night, originally G$47,101 GYD
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Guest favorite
Guest favorite
Home in Mount Sterling
THE DOLLY - Cozy, Bright Home in Historic Downtown
1 queen bed
1 queen bed
Apr 27 – May 2
Apr 27 – May 2
G$18,043 GYD
night
G$18,043 GYD per night
4.96 out of 5 average rating, 139 reviews
4.96 (139)
Guest favorite
Guest favorite
Cabin in Mount Sterling
The Honey Hut, Think of “ On Golden Pond"
2 beds
2 beds
Apr 21 – 26
Apr 21 – 26
G$40,725 GYD
night
G$40,725 GYD per night
4.96 out of 5 average rating, 202 reviews
4.96 (202)
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