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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₹86,626 for 5 nights

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Top guest favourite
Guest house in Winchester
Carriage House Gardenside
Free cancellation
1–6 Aug
₹35,977 for 5 nights
4.97 out of 5 average rating, 91 reviews
Flat in Winchester
Whimsical Winchester Apartment!
Free cancellation
2–7 Aug
₹34,570 for 5 nights
4.85 out of 5 average rating, 34 reviews
Guest favourite
Home in Winchester
Cute 2 Story Home in Winchester
Free cancellation
1–6 Aug
₹97,128 for 5 nights
4.93 out of 5 average rating, 45 reviews
Guest favourite
Home in Winchester
The Winchester
Free cancellation
1–6 Aug
₹88,436 for 5 nights
4.86 out of 5 average rating, 36 reviews
Home in Winchester
The Winchester 2
Free cancellation
1–6 Aug
₹88,436 for 5 nights
4.64 out of 5 average rating, 22 reviews
Top guest favourite
Home in Winchester
College Park Getaway
Free cancellation
1–6 Aug
₹89,907 for 5 nights
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Flat in Winchester
The Carriage Inn - 1-bdrm apt in historic downtown
1 queen bed
7–12 Aug
₹47,735 for 5 nights
4.94 out of 5 average rating, 98 reviews
Guest favourite
Loft in Winchester
Stylish Loft Historic Downtown 2Bdrm Winchester KY
Free cancellation
1–6 Aug
₹1,01,199 for 5 nights
4.96 out of 5 average rating, 85 reviews
Guest favourite
Room in Lexington
Stay with KellyFederal government,
Quiet Home in Quiet Neighborhood
9–14 Aug
₹21,104 for 5 nights
4.9 out of 5 average rating, 90 reviews
Superhost
Farm stay in Winchester
The Winchester Retreat
Free cancellation
10–15 Aug
₹49,745 for 5 nights
4.82 out of 5 average rating, 121 reviews
Cabin in Mount Sterling
Rustic Mt. Sterling Cabin1 Near Downtown • Pets OK
Free cancellation
1–6 Aug
₹57,081 for 5 nights
New place to stay
Flat in Winchester
The Perch - NEW / Downtown!
Free cancellation
1–6 Aug
₹58,881 for 5 nights
4.62 out of 5 average rating, 21 reviews
Top guest favourite
Guest suite in Lexington
A SuiteHart Stay In The Bluegrass
Free cancellation
8–13 Aug
₹39,696 for 5 nights
4.99 out of 5 average rating, 375 reviews
Guest favourite
Cabin in Irvine
Rustic Country cabin in the woods
Free cancellation
5–10 Aug
₹31,656 for 5 nights
4.92 out of 5 average rating, 100 reviews
Hotel in Lexington
Simple Comfort | Golf. Laundry Room. Free Parking.
Free cancellation
1–6 Aug
₹19,202 for 5 nights
New place to stay
Guest favourite
Loft in Winchester
Artist’s Loft 2Bdr Winchester, near Lexington KY
Free cancellation
9–14 Aug
₹94,063 for 5 nights
5.0 out of 5 average rating, 41 reviews
Guest favourite
Room in Versailles
Stay with JulieHosting for 7 years,
Downtown Historic Home
9–14 Aug
₹27,435 for 5 nights
4.92 out of 5 average rating, 322 reviews
Top guest favourite
Barn in Clay City
The Lodge 3 bedroom 2 bath barndo in wooded area
4 beds
1–6 Aug
₹1,43,064 for 5 nights
5.0 out of 5 average rating, 5 reviews