Search results; Over 1,000 homes in Winchester

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Home in Winchester
River Relaxation - Riverfront Home in Winchester
6 guests3 bedrooms3 beds3 bathrooms
24–29 Aug
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24–29 Aug
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₹75,450 for 5 nights

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Flat in Winchester
Whimsical Winchester Apartment!
1 queen bed
23–28 Aug
₹31,497 for 5 nights
4.86 out of 5 average rating, 35 reviews
Superhost
Farm stay in Winchester
The Winchester Retreat
1 bed
22–27 Aug
₹50,131 for 5 nights
4.81 out of 5 average rating, 129 reviews
Top guest favourite
Flat in Winchester
The Carriage Inn - 1-bdrm apt in historic downtown
1 queen bed
24–29 Aug
₹48,106 for 5 nights
4.94 out of 5 average rating, 102 reviews
Guest favourite
Home in Winchester
Cute 2 Story Home in Winchester
4 beds
26–31 Aug
₹99,013 for 5 nights
4.94 out of 5 average rating, 48 reviews
Top guest favourite
Guest house in Winchester
Carriage House Gardenside
1 king bed
2–7 Sept
₹39,498 for 5 nights
4.97 out of 5 average rating, 92 reviews
Top guest favourite
Home in Winchester
Cozy Cottage
1 queen bed
20–25 Sept
₹35,447 for 5 nights
4.91 out of 5 average rating, 831 reviews
Guest favourite
Home in Winchester
The Winchester
5 beds
13–18 Sept
₹89,122 for 5 nights
4.86 out of 5 average rating, 37 reviews
Flat in Winchester
2nd Story Historic Downtown 2 BR w Modern Comforts
2 queen beds
23–28 Aug
₹48,005 for 5 nights
4.66 out of 5 average rating, 110 reviews
Home in Winchester
The Winchester 2
5 beds
24–29 Aug
₹89,122 for 5 nights
4.68 out of 5 average rating, 25 reviews
Guest favourite
Room in Lexington
Stay with KellyFederal government,
Quiet Home in Quiet Neighborhood
23–28 Aug
₹21,268 for 5 nights
4.91 out of 5 average rating, 96 reviews
Guest favourite
Home in Winchester
College Park Getaway
3 beds
6–11 Sept
₹1,08,872 for 5 nights
4.88 out of 5 average rating, 8 reviews
Superhost
Loft in Winchester
Stylish Loft Historic Downtown 2Bdrm Winchester KY
2 beds
21–26 Aug
₹1,01,984 for 5 nights
4.95 out of 5 average rating, 87 reviews
Guest favourite
Loft in Winchester
Artist’s Loft 2Bdr Winchester, near Lexington KY
2 king beds
5–10 Sept
₹1,01,984 for 5 nights
5.0 out of 5 average rating, 42 reviews
Top guest favourite
Farm stay in Winchester
*2Rm Farm Cottage*King Bed*5min DT Winchester
2 beds
24–29 Aug
₹67,246 for 5 nights
5.0 out of 5 average rating, 76 reviews
Superhost
Shipping container in Lexington
Shipping Container Cabin - Tuck Jr
1 bed
22–27 Aug
₹44,982 for 5 nights
4.8 out of 5 average rating, 5 reviews
Guest favourite
Flat in Clay City
Gran's Guest House RRG! Back to School Specials!
1 queen bed
21–26 Aug
₹39,417 for 5 nights
4.87 out of 5 average rating, 63 reviews
Guest favourite
Guest house in Lexington
Cozy studio with private pool and firepit
2 beds
9–14 Sept
₹54,385 for 5 nights
4.89 out of 5 average rating, 281 reviews
Guest favourite
Cabin in Irvine
Mountain Tiny Home ~ Outdoor kitchen ~ Tin Cantina
2 beds
21–26 Aug
₹43,690 for 5 nights
5.0 out of 5 average rating, 9 reviews