Holiday rentals 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
Cottage in Shepherdstown
4.96 out of 5 average rating, 188 reviewsThe GW Hollida Cottage of Shepherdstown
Guest favourite
Guest house in Round Hill
4.98 out of 5 average rating, 380 reviewsPrivate Carriage House
Guest favourite
Home in Inwood
4.89 out of 5 average rating, 558 reviewsArden House, Inwood WV
Guest favourite
Farm stay in Round Hill
4.93 out of 5 average rating, 352 reviewsCome and get your goat on!
Guest favourite
Guest suite in Winchester
4.79 out of 5 average rating, 280 reviewsSafe, cozy oasis with private living & bath.
Guest favourite
Flat in Winchester
4.94 out of 5 average rating, 52 reviewsNewly repurposed Historic Home in Winchester VA!
Guest favourite
Flat in Winchester
4.97 out of 5 average rating, 77 reviewsHistoric Wisteria House on Old Town Walking Mall
Guest favourite
Home in Winchester
4.92 out of 5 average rating, 12 reviewsCabin in Historic Old Town Winchester
Quick stats about holiday rentals in Winchester
Total rentals
90 properties
Wifi availability
90 properties include access to wifi
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
6T reviews
Destinations to explore
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- Monthly Rentals Winchester
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