Search results; Over 1,000 homes in Winchester

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Superhost
Cottage in Winchester
Life is Better On The River
6 guests2 bedrooms3 beds2 bathrooms
6–11 Sept
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6–11 Sept
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₹1,24,964 for 5 nights

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Guest favourite
Guest house in Winchester
Carriage House on the Park
1 queen bed
1–6 Sept
₹36,048 for 5 nights
4.93 out of 5 average rating, 204 reviews
Flat in Winchester
Whimsical Winchester Apartment!
1 queen bed
21–26 Aug
₹33,196 for 5 nights
4.86 out of 5 average rating, 35 reviews
Superhost
Farm stay in Winchester
The Winchester Retreat
1 bed
16–21 Aug
₹50,405 for 5 nights
4.8 out of 5 average rating, 126 reviews
Top guest favourite
Flat in Winchester
The Carriage Inn - 1-bdrm apt in historic downtown
1 queen bed
11–16 Aug
₹48,369 for 5 nights
4.94 out of 5 average rating, 102 reviews
Top guest favourite
Home in Winchester
Cozy Cottage
1 queen bed
15–20 Sept
₹35,640 for 5 nights
4.91 out of 5 average rating, 829 reviews
Guest favourite
Home in Winchester
Cute 2 Story Home in Winchester
4 beds
2–7 Sept
₹1,03,841 for 5 nights
4.94 out of 5 average rating, 47 reviews
Guest favourite
Home in Winchester
The Winchester
5 beds
12–17 Aug
₹89,609 for 5 nights
4.86 out of 5 average rating, 37 reviews
Guest favourite
Loft in Winchester
Stylish Loft Historic Downtown 2Bdrm Winchester KY
2 beds
18–23 Aug
₹95,311 for 5 nights
4.96 out of 5 average rating, 85 reviews
Home in Winchester
The Winchester 2
5 beds
14–19 Aug
₹89,609 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
15–20 Aug
₹21,384 for 5 nights
4.9 out of 5 average rating, 93 reviews
Guest favourite
Loft in Winchester
Artist’s Loft 2Bdr Winchester, near Lexington KY
2 king beds
17–22 Aug
₹88,082 for 5 nights
5.0 out of 5 average rating, 41 reviews
Guest favourite
Home in Winchester
College Park Getaway
3 beds
14–19 Aug
₹86,567 for 5 nights
4.88 out of 5 average rating, 8 reviews
Top guest favourite
Farm stay in Winchester
*2Rm Farm Cottage*King Bed*5min DT Winchester
2 beds
11–16 Aug
₹53,241 for 5 nights
5.0 out of 5 average rating, 75 reviews
Top guest favourite
Room in Lexington
Stay with MarkRetired,
Lexington Home for Bluegrass Adventuresb
17–22 Aug
₹29,225 for 5 nights
4.96 out of 5 average rating, 776 reviews
Guest favourite
Flat in Clay City
Gran's Guest House RRG! Back to School Specials!
1 queen bed
11–16 Aug
₹39,632 for 5 nights
4.87 out of 5 average rating, 62 reviews
Guest favourite
Guest house in Lexington
Cozy studio with private pool and firepit
2 beds
19–24 Aug
₹52,544 for 5 nights
4.89 out of 5 average rating, 277 reviews
Flat in Winchester
The Perch - NEW / Downtown!
2 beds
12–17 Aug
₹57,738 for 5 nights
4.62 out of 5 average rating, 21 reviews
Top guest favourite
Farm stay in Winchester
LenMar Farm Country Stay near Lexington KY
3 beds
25–30 Aug
₹55,090 for 5 nights
4.92 out of 5 average rating, 159 reviews