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Check prices for these dates

In two weeks
5 Sept - 7 Sept
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Featured Condo Rentals in Winchester

Our top choices for Winchester condo rentals

Cozy 2-bedroom condo in charming Stephens City
Property grounds

Cozy 2-bedroom condo in charming Stephens City

10.0 out of 10, Exceptional, (1)
"This was the perfect location for our little get away. We had Easter lunch, played games, and stayed in a very clean nice place!!"
The price is AU$396
includes taxes & fees
3 Sept - 4 Sept
Cozy 2-bedroom condo in charming Stephens City
Upscale Walkup Apartment in the Heart of Historic Charles Town, WV
Interior

Upscale Walkup Apartment in the Heart of Historic Charles Town, WV

10.0 out of 10, Exceptional, (1)
"My wife and I wanted to get away for a quick n easy Valentine's Day and so I tried VRBO to find something relatively close and reasonable. We both like to hit venture and try new things, and hit the Casino if there is one.So often we've visited the Charles Town Casino and Horse Track, and didn't even realize there was an entire historic downtown area. Talk about a surprise and a quaint and lovely area. I can only hope it continues to grow and prosper. The downtown coffee shop we walked to...
Upscale Walkup Apartment in the Heart of Historic Charles Town, WV
Historic District Downtown Winchester
Interior

Historic District Downtown Winchester

9.8 out of 10, Exceptional, (8)
"We love coming here. Great place and great location."
Historic District Downtown Winchester
Take a Walk Around The Lake - Close to many attractions and Airport.
Property grounds

Take a Walk Around The Lake - Close to many attractions and Airport.

Take a Walk Around The Lake - Close to many attractions and Airport.
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

Red Roof Inn Winchester, VA

Red Roof Inn Winchester, VA

10/10 Excellent
"It was reasonably priced with everything needed for a good night’s sleep. I didn’t bring my pet, but I was happy to hear that he is welcome too!"
Kathryn 1-night trip
Posted 22 hours ago
Red Roof Inn Winchester, VA