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 favourite
Loft in Purcellville
4.99 out of 5 average rating, 294 reviews"When Pigs Fly" Airbnb Most Hospitable Host in VA
Guest favourite
Cabin in Lost River
4.96 out of 5 average rating, 115 reviewsRustic and stylish mountain getaway
Superhost
Cabin in Gerrardstown
4.88 out of 5 average rating, 186 reviewsModern Treetop Cabin with Views and Nearby Creek
Guest favourite
Guest suite in Shepherdstown
4.95 out of 5 average rating, 572 reviewsHistoric Scrabble, Shepherdstown
Guest favourite
Cottage in Strasburg
4.95 out of 5 average rating, 390 reviewsThe Cottage at the Barb Farm
Guest favourite
Apartment in Winchester
4.97 out of 5 average rating, 79 reviewsHistoric Wisteria House on Old Town Walking Mall
Guest favourite
Apartment in Winchester
4.93 out of 5 average rating, 54 reviewsNewly repurposed Historic Home in Winchester VA!
Guest favourite
Home in Winchester
4.93 out of 5 average rating, 27 reviewsMisty Meadow has quite setting in the country.
Quick stats about vacation 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
6K reviews
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