filters

Search results; Over 1,000 homes in Winchester

Photo 1 of 29
Guest favourite
Cottage in Winchester
Life is Better On The River
2 bedrooms, 3 beds, 2 private bathrooms
12–17 Oct
,
4.88 out of 5 average rating, 139 reviews
Photo 1 of 23
Guest favourite
Loft in Winchester
Stylish Loft 2Bdrm Winchester ky near Lexington
2 bedrooms, 2 beds
23–28 Sept
4.96 out of 5 average rating, 104 reviews
Photo 1 of 29
Home in Winchester
Aisling House - Historic Hospitality
7 bedrooms, 8 beds
27 Sept – 2 Oct
New place to stay
Photo 1 of 29
Guest favourite
Loft in Winchester
Artist’s Loft 2Bdr Winchester ky near Lexington
2 bedrooms, 2 king beds
21–26 Sept
5.0 out of 5 average rating, 53 reviews
Photo 1 of 29
Top guest favourite
Farm stay in Winchester
Family Farm Winchester/Lexington 20 min.*Game Room
4 bedrooms, 8 beds
20–25 Sept
4.97 out of 5 average rating, 147 reviews
Photo 1 of 8
Top guest favourite
Home in Winchester
Cozy Cottage
1 bedroom, 1 queen bed
2–7 Nov
4.92 out of 5 average rating, 969 reviews
Photo 1 of 18
Top guest favourite
Flat in Winchester
The Carriage Inn - 1-bdrm apt in historic downtown
1 bedroom, 1 queen bed
28 Sept – 3 Oct
4.94 out of 5 average rating, 124 reviews
Photo 1 of 24
Guest favourite
Guest house in Winchester
Carriage House on the Park
1 bedroom, 1 queen bed
24–29 Sept
4.92 out of 5 average rating, 230 reviews
Photo 1 of 23
Top guest favourite
Farm stay in Winchester
LenMar Farm Country Stay near Lexington KY
2 bedrooms, 3 beds
17–22 Nov
4.94 out of 5 average rating, 197 reviews
Photo 1 of 26
Top guest favourite
Farm stay in Winchester
*2Rm Farm Cottage*King Bed*5min DT Winchester
1 bedroom, 2 beds
19–24 Sept
5.0 out of 5 average rating, 100 reviews
Photo 1 of 21
Guest favourite
Flat in Winchester
RiverView 1 - Enjoy the view.
1 bedroom, 3 beds
20–25 Sept
4.8 out of 5 average rating, 71 reviews
Photo 1 of 23
Guest favourite
Cabin in Winchester
Historic Cabin - Farm - Near RRG, Lex, local music
2 bedrooms, 3 beds
28 Sept – 3 Oct
4.92 out of 5 average rating, 91 reviews
Photo 1 of 29
Top guest favourite
Home in Winchester
Right Angle Country*Remote*Hot Tub~NO Cleaning FEE
2 bedrooms, 4 beds
27 Sept – 2 Oct
4.99 out of 5 average rating, 95 reviews
Photo 1 of 22
Top guest favourite
Home in Winchester
Peacock Ranch House - Lexington and Winchester
3 bedrooms, 3 queen beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 35 reviews
Photo 1 of 17
Guest favourite
Home in Winchester
Bloomfield Garden House
2 bedrooms, 2 beds
26–31 May
5.0 out of 5 average rating, 14 reviews
Photo 1 of 12
Guest favourite
Home in Lexington
Country cottage in the heart of the Bluegrass
3 bedrooms, 3 beds
28 Sept – 3 Oct
4.94 out of 5 average rating, 31 reviews
Photo 1 of 29
Guest favourite
Home in Winchester
Comfortable Bluegrass Living
2 bedrooms, 3 beds
1–6 Nov
5.0 out of 5 average rating, 17 reviews
Photo 1 of 29
Guest favourite
Townhouse in Lexington
Bounce to Hamburg/I-75/St. Joe E
2 bedrooms, 2 beds
27 Sept – 2 Oct
4.94 out of 5 average rating, 84 reviews
Photo 1 of 17
Top guest favourite
Home in Winchester
River Duplex (private upstairs entrance)
2 bedrooms, 3 beds
28 Sept – 3 Oct
4.97 out of 5 average rating, 64 reviews