Villas in Winchester

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Check prices for these dates

Next weekend
1 Aug - 3 Aug
In two weeks
8 Aug - 10 Aug
In one month
22 Aug - 24 Aug
In two months
19 Sept - 21 Sept

Featured Villas in Winchester

Elegant Paris Manor w/ Private Pool!
Interior

Elegant Paris Manor w/ Private Pool!

3.0 star property
Elegant Paris Manor w/ Private Pool!
Historic Virginia Wine Country Villa w/ Pool, Yard
TV, fireplace, DVD player, iPod dock

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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Top Winchester Hotel Reviews

Comfort Inn & Suites

Comfort Inn & Suites

10/10 Excellent
"The hotel was very nice. Clean, friendly staff, close to dining options, and a good breakfast. "
Elizabeth 1-night trip
Posted 22 hours ago
Comfort Inn & Suites

Frequently asked questions

Why book your villa in Winchester with Expedia?
With Expedia, it's easy to find your ideal villa in Winchester. Holidaying with the family? Take advantage of our filters to look for stays with amenities like a pool. If you're sticking to a budget, click on how much you want to spend and your preferred star rating. We'll help you find the right stay that gels with your taste and style.
How can I find cheap villas in Winchester?
With Expedia's filter tool, comparing cheap villas in Winchester has never been easier. To find properties that give you the most bang for your buck, narrow your search by budget, star rating and amenities.
What is there to do near my villa in Winchester?
Whatever you love doing, Winchester has plenty of things to keep you on the move. Rock Harbour Golf Course, The Kernstown Battlefield and Museum of the Shenandoah Valley are on many visitors' lists. Don't head home without exploring Apple Blossom Mall, Jim Barnett Park and Handley Regional Library either. With Expedia's Winchester hotel deals, you'll be able to discover even more renowned attractions like these with the money you save.