Holiday houses in Winchester
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Top-rated holiday rentals in Winchester
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Winchester holiday rentals
Other great holiday rentals in Winchester
Guest favourite
Cabin in Lost River
4.96 out of 5 average rating, 115 reviewsRustic and stylish mountain getaway
Guest favourite
Cabin in Lost City
4.96 out of 5 average rating, 254 reviewsHigh View Hideaway - A Cozy Lost River Cabin
Guest favourite
Apartment in Winchester
4.97 out of 5 average rating, 79 reviewsHistoric Wisteria House on Old Town Walking Mall
Guest favourite
Home in Winchester
4.93 out of 5 average rating, 27 reviewsMisty Meadow has quite setting in the country.
Guest favourite
Apartment in Winchester
4.93 out of 5 average rating, 54 reviewsNewly repurposed Historic Home in Winchester VA!
Guest favourite
Place to stay in Winchester
4.89 out of 5 average rating, 54 reviewsCrash Landing
Guest favourite
Home in Winchester
4.92 out of 5 average rating, 13 reviewsCabin in Historic Old Town Winchester
Guest favourite
Condo in Winchester
4.98 out of 5 average rating, 53 reviewsHistoric District Downtown Winchester
Quick stats about holiday rentals in Winchester
Total rentals
90 properties
Wi-Fi availability
90 properties include access to Wi-Fi
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
6K reviews
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