Villas in Winchester

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Featured Villas in Winchester

Elegant Paris Manor w/ Private Pool!
Property grounds
Elegant Paris Manor w/ Private Pool!
3.0 star property
Elegant Paris Manor w/ Private Pool!
Historic Virginia Wine Country Villa w/ Pool, Yard
Outdoor dining
Historic Virginia Wine Country Villa w/ Pool, Yard
3.0 star property
Historic Virginia Wine Country Villa w/ Pool, Yard
Stunning Former Winery w/ Pool & Mtn Views!
Interior
Stunning Former Winery w/ Pool & Mtn Views!
3.0 star property
Stunning Former Winery w/ Pool & Mtn Views!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Winchester

Frequently asked questions

Why book your villa in Winchester with Expedia?
We think holiday time shouldn’t be hard, so if you’re on the lookout for villas at a competitive rate, Expedia delivers. Save those pennies and go for an all-inclusive stay, or splurge on a deluxe villa to spoil your loved ones. Use our search filters to find a property in Winchester that matches your needs.
How can I find cheap villas in Winchester?
Expedia is here to help you look for cheap villas in Winchester. Use our filter tool to select amenities, star rating and budget to refine your search and find the perfect stay in a couple of quick clicks.
What is there to do near my villa in Winchester?
Winchester has enough sights and activities to entertain you for weeks (or months!), starting with Museum of the Shenandoah Valley. Shenandoah Valley Discovery Museum, Bright Box Theatre and Winchester Little Theatre are other wonderful attractions. If you’re staying a while longer, Shenandoah University and Jim Barnett Park are worthwhile additions to your itinerary.