Search results; Over 1,000 homes in Winchester

Guest favourite
Flat in Winchester
Whimsical Winchester Apartment!
1 bedroom, 1 bed, 1 bathroom
19–24 Oct
₹36,799 for 5 nights
,
4.86 out of 5 average rating, 37 reviews
Guest favourite
Farm stay in Winchester
The Winchester Retreat
1 bed
4–9 Oct
₹50,881 for 5 nights
4.81 out of 5 average rating, 136 reviews
Top guest favourite
Home in Winchester
Cute 2 Story Home in Winchester
4 beds
5–10 Oct
₹96,962 for 5 nights
4.94 out of 5 average rating, 48 reviews
Flat in Winchester
The Winchester Cozy One Bedroom!
1 queen bed
6–11 Oct
₹32,071 for 5 nights
4.66 out of 5 average rating, 35 reviews
Guest favourite
Home in Winchester
The Winchester
5 beds
12–17 Oct
₹90,456 for 5 nights
4.84 out of 5 average rating, 38 reviews
Flat in Winchester
The Perch - NEW / Downtown!
2 beds
1–6 Oct
₹63,052 for 5 nights
4.52 out of 5 average rating, 23 reviews
Top guest favourite
Flat in Winchester
The Carriage Inn - 1-bdrm apt in historic downtown
1 queen bed
5–10 Oct
₹48,826 for 5 nights
4.94 out of 5 average rating, 104 reviews
Top guest favourite
Home in Winchester
Cozy Cottage
1 queen bed
27 Oct – 1 Nov
₹35,977 for 5 nights
4.91 out of 5 average rating, 844 reviews
Guest favourite
Guest house in Winchester
Carriage House on the Park
1 queen bed
4–9 Nov
₹41,116 for 5 nights
4.93 out of 5 average rating, 206 reviews
Home in Winchester
The Winchester 2
5 beds
12–17 Oct
₹87,372 for 5 nights
4.7 out of 5 average rating, 27 reviews
Top guest favourite
Loft in Winchester
Artist’s Loft 2Bdr Winchester ky near Lexington
2 king beds
5–10 Oct
₹88,914 for 5 nights
5.0 out of 5 average rating, 42 reviews
Top guest favourite
Guest suite in Lexington
A SuiteHart Stay In The Bluegrass
1 king bed
26–31 Oct
₹51,395 for 5 nights
4.99 out of 5 average rating, 390 reviews
Guest favourite
Room in Lexington
Stay with Charbel
Cute little place to stay
4–9 Oct
₹18,503 for 5 nights
5.0 out of 5 average rating, 6 reviews
Superhost
Guest house in Lexington
Cozy studio with private pool and firepit
2 beds
4–9 Oct
₹47,901 for 5 nights
4.89 out of 5 average rating, 288 reviews
Guest favourite
Treehouse in Georgetown
★Escape & Relax ~ Breathtaking Creekside Getaway★
3 beds
19–24 Oct
₹97,651 for 5 nights
4.94 out of 5 average rating, 289 reviews
Guest favourite
Cabin in Irvine
Rustic Country cabin in the woods
4 beds
2–7 Oct
₹32,379 for 5 nights
4.92 out of 5 average rating, 108 reviews
Superhost
Cabin in Stanton
Suspended SkyView Cabin Near RRG
26–31 Oct
₹1,15,023 for 5 nights
4.85 out of 5 average rating, 98 reviews
Guest favourite
Flat in Richmond
Interstate 75 Apartment
2 queen beds
26–31 Oct
₹56,021 for 5 nights
5.0 out of 5 average rating, 39 reviews
Guest favourite
Loft in Winchester
Stylish Loft 2Bdrm Winchester ky near Lexington
2 beds
13–18 Dec
₹96,211 for 5 nights
4.95 out of 5 average rating, 87 reviews