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Search results; Over 1,000 places in Winchester
Over 1,000 places in Winchester
Guest favorite
Guest favorite
Home in Winchester
Cozy Cottage
1 queen bed
1 queen bed
May 12 – 17
May 12 – 17
G$14,303 GYD
night
G$14,303 GYD per night
4.91 out of 5 average rating, 672 reviews
4.91 (672)
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
G$30,186 GYD
G$25,848 GYD
night
G$25,848 GYD per night, originally G$30,186 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 19 – 24
Apr 19 – 24
G$20,469 GYD
night
G$20,469 GYD per night
4.93 out of 5 average rating, 73 reviews
4.93 (73)
Guest favorite
Guest favorite
Apartment in Winchester
Whimsical Winchester Apartment!
1 queen bed
1 queen bed
Apr 28 – May 3
Apr 28 – May 3
G$12,017 GYD
night
G$12,017 GYD per night
4.93 out of 5 average rating, 14 reviews
4.93 (14)
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
G$20,378 GYD
night
G$20,378 GYD per night
4.65 out of 5 average rating, 80 reviews
4.65 (80)
Guest favorite
Guest favorite
Guesthouse in Winchester
Escape and unwind in the country
2 beds
2 beds
May 6 – 11
May 6 – 11
G$20,262 GYD
night
G$20,262 GYD per night
4.98 out of 5 average rating, 174 reviews
4.98 (174)
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$22,257 GYD
G$18,567 GYD
night
G$18,567 GYD per night, originally G$22,257 GYD
5.0 out of 5 average rating, 54 reviews
5.0 (54)
Superhost
Superhost
Farm stay in Winchester
The Winchester Retreat
1 bed
1 bed
Apr 21 – 26
Apr 21 – 26
G$27,986 GYD
G$23,600 GYD
night
G$23,600 GYD per night, originally G$27,986 GYD
4.86 out of 5 average rating, 43 reviews
4.86 (43)
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
G$24,172 GYD
night
G$24,172 GYD per night
4.93 out of 5 average rating, 106 reviews
4.93 (106)
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$35,809 GYD
night
G$35,809 GYD per night
4.98 out of 5 average rating, 57 reviews
4.98 (57)
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$19,647 GYD
night
G$19,647 GYD per night
4.95 out of 5 average rating, 159 reviews
4.95 (159)
Apartment in Winchester
2nd Floor Historic Downtown Updated 1 Bedroom
1 queen bed
1 queen bed
Apr 19 – 24
Apr 19 – 24
G$20,711 GYD
night
G$20,711 GYD per night
4.27 out of 5 average rating, 15 reviews
4.27 (15)
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$19,277 GYD
night
G$19,277 GYD per night
4.92 out of 5 average rating, 99 reviews
4.92 (99)
Guest favorite
Guest favorite
Home in Winchester
Cute 2 Story Home in Winchester
4 beds
4 beds
Jun 21 – 26
Jun 21 – 26
G$43,498 GYD
night
G$43,498 GYD per night
5.0 out of 5 average rating, 13 reviews
5.0 (13)
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$31,194 GYD
night
G$31,194 GYD per night
4.88 out of 5 average rating, 42 reviews
4.88 (42)
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$60,154 GYD
G$50,637 GYD
night
G$50,637 GYD per night, originally G$60,154 GYD
4.97 out of 5 average rating, 87 reviews
4.97 (87)
Superhost
Superhost
Home in Winchester
The Winchester 2
5 beds
5 beds
May 5 – 10
May 5 – 10
G$47,086 GYD
G$38,731 GYD
night
G$38,731 GYD per night, originally G$47,086 GYD
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Superhost
Superhost
Home in Winchester
River Relaxation -3king beds
3 beds
3 beds
May 18 – 23
May 18 – 23
G$43,096 GYD
night
G$43,096 GYD per night
4.82 out of 5 average rating, 39 reviews
4.82 (39)
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