Discover a selection of 1,000 vacation rentals in City of Winchester that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $124 per night, and houses and condos are popular options for a stay in City of Winchester. Either way, you'll find a rental for everyone's needs.
AsyncDestinationUrgency
Top rated rentals — City of Winchester
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy

How many vacation rentals are available around City of Winchester?

Our 2021 property listings offer a large selection of 803 vacation rentals around City of Winchester. From 404 house rentals to 340 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.