Vacation Rentals in Winchester, VA

Explore 27 vacation rentals near Winchester, Virginia. Whether you’re a tourist or on a staycation, there’s plenty of things to do and restaurants to try around the city. If you’re looking to take a trip to Winchester, you can see photos of Winchester vacation rentals, view amenities and features, browse by specific property types, and more. Use our interactive map to find Winchester vacation rentals in specific areas. Whether you’re looking for a Winchester staycation, weekend getaway, or a long vacation, we’ve got you covered. Use the date filters at the top to select your travel dates and view availability. The lowest vacation rental price in Winchester is $34 per night and the highest price is $304 per night.

2 of the vacation rentals near Winchester are apartments or condos. The average bathroom count for this property type is 2. The median price for these vacation units is $90 per night. There are currently 1 vacation units under this price. 6 of the vacation rentals near Winchester are houses. The average bathroom count for a vacation house near Winchester is 2. The average price for vacation houses near Winchester is $129 per night. There are 3 vacation homes under this price. The most common amenities for vacation rentals near Winchester are: furnished, air conditioning, and wifi. To find vacation properties that might be a good option for large groups or families, use our filters for bedroom count, bathroom count and more.