Holiday rentals in Winchester
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Top-rated holiday rentals in Winchester
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Holiday rentals for every style
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Popular amenities for Winchester holiday rentals
Other great holiday rentals in Winchester
Flat in Winchester
4.93 out of 5 average rating, 73 reviewsThe Carriage Inn - 1-bdrm apt in historic downtown
29 Nov – 6 Dec
Loft in Winchester
4.98 out of 5 average rating, 58 reviewsStylish Loft Historic Downtown 2Bdrm Winchester KY
12–19 Jul
Farm stay in Winchester
4.88 out of 5 average rating, 42 reviewsRenovated historic home on working cattle farm
26 Sept – 3 Oct
Farm stay in Winchester
4.84 out of 5 average rating, 45 reviewsThe Winchester Retreat
16–23 Sept
Loft in Winchester
5.0 out of 5 average rating, 13 reviewsHanna’s 1,400 SQ FT Downtown Royal Retreat Loft
28 Oct – 4 Nov
Home in Winchester
4.86 out of 5 average rating, 14 reviewsCute 2 Story Home in Winchester
30 Sept – 7 Oct
Farm stay in Winchester
5.0 out of 5 average rating, 54 reviewsDT Winchester 5 min.*2Rm Farm Cottage-Comfy King*
10–17 Aug
Cabin in Waco
5.0 out of 5 average rating, 58 reviewsStunning Cedar Cabin, Hot Tub, Amazing Views!
8–15 Jul
Quick stats about holiday 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
£40 before taxes and fees
Destinations to explore
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