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.
Vacation rentals for every style
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Popular amenities for Winchester vacation rentals
Other great vacation rentals in Winchester
Apartment in Winchester
4.93 out of 5 average rating, 73 reviewsThe Carriage Inn - 1-bdrm apt in historic downtown
Jul. 1 – 8
Loft in Winchester
4.98 out of 5 average rating, 58 reviewsStylish Loft Historic Downtown 2Bdrm Winchester KY
Sep. 5 – 12
Farm stay in Winchester
4.88 out of 5 average rating, 42 reviewsRenovated historic home on working cattle farm
Feb. 28 – Mar. 7
Farm stay in Winchester
4.84 out of 5 average rating, 45 reviewsThe Winchester Retreat
Dec. 23 – 30
Loft in Winchester
5.0 out of 5 average rating, 13 reviewsHanna’s 1,400 SQ FT Downtown Royal Retreat Loft
Sep. 22 – 29
Farm stay in Winchester
5.0 out of 5 average rating, 54 reviewsDT Winchester 5 min.*2Rm Farm Cottage-Comfy King*
Aug. 10 – 17
Home in Winchester
4.86 out of 5 average rating, 14 reviewsCute 2 Story Home in Winchester
Oct. 2 – 9
Cabin in Waco
5.0 out of 5 average rating, 58 reviewsStunning Cedar Cabin, Hot Tub, Amazing Views!
Dec. 14 – 21
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
$68 CAD before taxes and fees
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