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Winchester
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Over 1,000 places in Winchester
Guest favorite
Guest favorite
Guesthouse in Winchester
Carriage House on the Park
1 queen bed
1 queen bed
Apr 1 – 6
Apr 1 – 6
$88
$78
night
$78 per night, originally $88
4.95 out of 5 average rating, 155 reviews
4.95 (155)
Guest favorite
Guest favorite
Loft in Winchester
Stylish Loft Historic Downtown 2Bdrm Winchester KY
2 beds
2 beds
Apr 1 – 6
Apr 1 – 6
$161
night
$161 per night
4.98 out of 5 average rating, 56 reviews
4.98 (56)
Home in Winchester
The Winchester 2
5 beds
5 beds
Apr 1 – 6
Apr 1 – 6
$191
$169
night
$169 per night, originally $191
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Guest favorite
Guest favorite
Home in Winchester
Cute 2 Story Home in Winchester
4 beds
4 beds
Jun 4 – 9
Jun 4 – 9
$180
night
$180 per night
5.0 out of 5 average rating, 12 reviews
5.0 (12)
Guest favorite
Guest favorite
Farm stay in Winchester
Family Farm Winchester/Lexington 20 min.*Game Room
8 beds
8 beds
Apr 13 – 18
Apr 13 – 18
$230
$187
night
$187 per night, originally $230
4.96 out of 5 average rating, 83 reviews
4.96 (83)
Guest favorite
Guest favorite
Apartment in Winchester
The Carriage Inn - 1-bdrm apt in historic downtown
1 queen bed
1 queen bed
Apr 15 – 20
Apr 15 – 20
$84
night
$84 per night
4.93 out of 5 average rating, 72 reviews
4.93 (72)
Guest favorite
Guest favorite
Guesthouse in Winchester
Escape and unwind in the country
2 beds
2 beds
Apr 29 – May 4
Apr 29 – May 4
$85
night
$85 per night
4.98 out of 5 average rating, 171 reviews
4.98 (171)
Home in Winchester
The Right Angle
4 beds
4 beds
Apr 1 – 6
Apr 1 – 6
$127
$95
night
$95 per night, originally $127
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Guest favorite
Guest favorite
Apartment in Winchester
The River House Floor 2 Getaway, w/a river view.
1 king bed
1 king bed
Apr 14 – 19
Apr 14 – 19
$81
night
$81 per night
4.93 out of 5 average rating, 96 reviews
4.93 (96)
Guest favorite
Guest favorite
Farm stay in Winchester
LenMar Farm Country Stay near Lexington KY
3 beds
3 beds
Jun 4 – 9
Jun 4 – 9
$112
night
$112 per night
4.93 out of 5 average rating, 101 reviews
4.93 (101)
Home in Winchester
Wi-Fi - Office Space - Full Gym Access - Park View
Apr 1 – 6
Apr 1 – 6
$199
$159
night
$159 per night, originally $199
New place to stay
New
Guest favorite
Guest favorite
Farm stay in Winchester
*Comfy King*2Rm Farm Cottage* DT Winchester 5 min.
2 beds
2 beds
Apr 13 – 18
Apr 13 – 18
$106
$84
night
$84 per night, originally $106
5.0 out of 5 average rating, 51 reviews
5.0 (51)
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, 41 reviews
4.88 (41)
Superhost
Superhost
Home in Winchester
River Relaxation -3king beds
3 beds
3 beds
Apr 6 – 11
Apr 6 – 11
$163
night
$163 per night
4.86 out of 5 average rating, 35 reviews
4.86 (35)
Guest favorite
Guest favorite
Loft in Winchester
Artist’s Loft 2Bdr Winchester, near Lexington KY
2 king beds
2 king beds
Jun 9 – 14
Jun 9 – 14
$147
night
$147 per night
5.0 out of 5 average rating, 24 reviews
5.0 (24)
Guest favorite
Guest favorite
Cottage in Winchester
Life is Better On The River (Hot Tub with a View)
3 beds
3 beds
Apr 14 – 19
Apr 14 – 19
$225
night
$225 per night
4.95 out of 5 average rating, 61 reviews
4.95 (61)
Guest favorite
Guest favorite
Home in Winchester
Peacock Ranch House - Lexington and Winchester
3 queen beds
3 queen beds
Apr 16 – 21
Apr 16 – 21
$241
night
$241 per night
5.0 out of 5 average rating, 22 reviews
5.0 (22)
Guest favorite
Guest favorite
Cabin in Mount Sterling
The Honey Hut, Think of “ On Golden Pond"
2 beds
2 beds
Apr 6 – 11
Apr 6 – 11
$177
night
$177 per night
4.95 out of 5 average rating, 199 reviews
4.95 (199)
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