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Check prices for these dates

Next weekend
May 9 - May 11
In two weeks
May 16 - May 18
In one month
May 30 - Jun 1
In two months
Jun 27 - Jun 29

Compare 5 Condo Rentals in Upperville with updated reviews, rates, and availability.

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 $230
includes taxes & fees
$211 per night
May 2 - May 3
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
Exterior

Historic District Downtown Winchester

9.8 out of 10, Exceptional, (8)
"Impeccably clean and modern within walking distance - (4 minutes) of downtown. Thanks for a great visit!"
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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Other property types in Upperville

Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
Outdoor dining

Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

10.0 out of 10, Exceptional, (83)
"This beautiful cabin has everything you need for a wonderful stay. My husband and I stayed here for our 44th anniversary while visiting local wineries. It was a perfect location."
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
18th Century Stone Cottage minutes from historic Middleburg
Exterior

18th Century Stone Cottage minutes from historic Middleburg

10.0 out of 10, Exceptional, (40)
"My husband and I stayed at Tim’s cottage in middleburg for one night to celebrate our 10th wedding anniversary. Tim had left a bottle of champagne and chocolate cake for us since he knew it was our anniversary, which was an incredibly thoughtful and kind gesture. The cottage was clean, cute and cozy and the location was incredibly convenient to wineries, breweries and downtown Middleburg. It was truly a staycation to remember!"
The price is $393
includes taxes & fees
$366 per night
May 8 - May 9
18th Century Stone Cottage minutes from historic Middleburg
Cozy Mountain Cabin w/ Steam Shower! Great for Couples.
Smart TV, DVD player, books, video library

Cozy Mountain Cabin w/ Steam Shower! Great for Couples.

10.0 out of 10, Exceptional, (64)
"Really nice house that was accurate to listing. Bathroom in particular was nicely furnished with a great shower room. Great view from the indoor deck area. Nice outdoor space with well-done landscaping and a fire pit. The property owner was also highly flexible with needs for my pet. I would recommend this property and would stay there again."
The price is $351
includes taxes & fees
$315 per night
May 27 - May 28
Cozy Mountain Cabin w/ Steam Shower! Great for Couples.
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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