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winchester ky
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Over 1,000 rooms in Winchester
Guest favorite
Guest favorite
Home in Winchester
Cozy Cottage
1 queen bed
1 queen bed
May 12 – 17
May 12 – 17
$60
night
$60 per night
4.91 out of 5 average rating, 672 reviews
4.91 (672)
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
$147
night
$147 per night
4.98 out of 5 average rating, 57 reviews
4.98 (57)
Apartment in Winchester
The Winchester Cozy One Bedroom!
1 queen bed
1 queen bed
Apr 30 – May 5
Apr 30 – May 5
$57
night
$57 per night
4.7 out of 5 average rating, 20 reviews
4.7 (20)
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
$129
night
$129 per night
4.88 out of 5 average rating, 42 reviews
4.88 (42)
Apartment in Winchester
2nd Story Historic Downtown 2 BR w Modern Comforts
2 queen beds
2 queen beds
Apr 28 – May 3
Apr 28 – May 3
$84
night
$84 per night
4.65 out of 5 average rating, 80 reviews
4.65 (80)
Guest favorite
Guest favorite
Home in Winchester
NEW Serene Country Refuge at The Right Angle
4 beds
4 beds
Apr 19 – 24
Apr 19 – 24
$129
$108
night
$108 per night, originally $129
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 19 – 24
Apr 19 – 24
$85
night
$85 per night
4.93 out of 5 average rating, 73 reviews
4.93 (73)
Guest favorite
Guest favorite
Home in Winchester
Cute 2 Story Home in Winchester
4 beds
4 beds
Jun 21 – 26
Jun 21 – 26
$180
night
$180 per night
5.0 out of 5 average rating, 13 reviews
5.0 (13)
Guest favorite
Guest favorite
Guesthouse in Winchester
Escape and unwind in the country
2 beds
2 beds
May 6 – 11
May 6 – 11
$85
night
$85 per night
4.98 out of 5 average rating, 174 reviews
4.98 (174)
Guest favorite
Guest favorite
Farm stay in Winchester
LenMar Farm Country Stay near Lexington KY
3 beds
3 beds
May 13 – 18
May 13 – 18
$100
night
$100 per night
4.93 out of 5 average rating, 106 reviews
4.93 (106)
Superhost
Superhost
Farm stay in Winchester
The Winchester Retreat
1 bed
1 bed
Apr 21 – 26
Apr 21 – 26
$120
$99
night
$99 per night, originally $120
4.86 out of 5 average rating, 43 reviews
4.86 (43)
Guest favorite
Guest favorite
Guesthouse in Winchester
Carriage House on the Park
1 queen bed
1 queen bed
May 22 – 27
May 22 – 27
$82
night
$82 per night
4.95 out of 5 average rating, 159 reviews
4.95 (159)
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
$93
$76
night
$76 per night, originally $93
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
$255
$210
night
$210 per night, originally $255
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
$178
night
$178 per night
4.82 out of 5 average rating, 39 reviews
4.82 (39)
Apartment in Winchester
2nd Floor Historic Downtown Updated 1 Bedroom
1 queen bed
1 queen bed
Apr 19 – 24
Apr 19 – 24
$85
night
$85 per night
4.27 out of 5 average rating, 15 reviews
4.27 (15)
Superhost
Superhost
Home in Winchester
The Winchester 2
5 beds
5 beds
May 5 – 10
May 5 – 10
$200
$160
night
$160 per night, originally $200
5.0 out of 5 average rating, 4 reviews
5.0 (4)
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
$172
night
$172 per night
4.96 out of 5 average rating, 202 reviews
4.96 (202)
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