Vacation rentals in Winchester
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Top-rated vacation rentals in Winchester
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Winchester vacation rentals
Other great vacation rentals in Winchester
Guest favorite
Apartment in Winchester
4.93 out of 5 average rating, 73 reviewsThe Carriage Inn - 1-bdrm apt in historic downtown
Jul 1 – 8
ﺩ.ﺇ356 per night
Guest favorite
Loft in Winchester
4.98 out of 5 average rating, 58 reviewsStylish Loft Historic Downtown 2Bdrm Winchester KY
Sep 5 – 12
ﺩ.ﺇ563 per night
Guest favorite
Farm stay in Winchester
4.88 out of 5 average rating, 42 reviewsRenovated historic home on working cattle farm
Feb 28 – Mar 7
ﺩ.ﺇ492 per night
Superhost
Farm stay in Winchester
4.84 out of 5 average rating, 45 reviewsThe Winchester Retreat
Dec 23 – 30
ﺩ.ﺇ415 per night
Guest favorite
Loft in Winchester
5.0 out of 5 average rating, 13 reviewsHanna’s 1,400 SQ FT Downtown Royal Retreat Loft
Sep 22 – 29
ﺩ.ﺇ494 per night
Guest favorite
Farm stay in Winchester
5.0 out of 5 average rating, 54 reviewsDT Winchester 5 min.*2Rm Farm Cottage-Comfy King*
Aug 10 – 17
ﺩ.ﺇ474 per night
Guest favorite
Home in Winchester
4.86 out of 5 average rating, 14 reviewsCute 2 Story Home in Winchester
Oct 2 – 9
ﺩ.ﺇ724 per night
Guest favorite
Cabin in Waco
5.0 out of 5 average rating, 58 reviewsStunning Cedar Cabin, Hot Tub, Amazing Views!
Dec 14 – 21
ﺩ.ﺇ550 per night
Quick stats about vacation rentals in Winchester
Total rentals
10 properties
Wifi availability
10 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Total number of reviews
1.2K reviews
Nightly prices starting at
ﺩ.ﺇ184 before taxes and fees
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