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Vacation Homes in Upperville

"Walkable to downtown historic Leesburg. Clean and super cute little house. Would stay again! "

$265 nightly

Aug 11 - Aug 12

Total includes taxes and fees

"The views are beautiful and the house was the perfect size for a group of 7 friends. We had a great time!"

"Our stay was great and really enjoyed the house. We had so much space to have our own time and then still be able to come together for meals and hanging in the hot tub. We now want to come back in the winter and go to the sledding hill right in front of the house! "

"Great and quiet location with all the amenities. Getting to the parking is a bit tricky but other than that great place to stay with family"

$289 nightly

Sep 3 - Sep 4

Total includes taxes and fees

"The house was beautiful, fully stocked, close to home and vineyards. It surpassed our expectations! Can’t wait to again. "

$530 nightly

Aug 12 - Aug 13

Total includes taxes and fees

"Four family members stayed for a four day weekend. The place was spotless when we arrived and all amenities are as described. The location is perfect for visiting Harpers Ferry, Shepherdstown, and Antietam. We had wonderful time."

$446 nightly

Aug 12 - Aug 13

Total includes taxes and fees

"Excelente propiedad "

$214 nightly

Aug 25 - Aug 26

Total includes taxes and fees

"We really enjoyed our stay at Bear Chase Manor! Amazing property, great pool, in a beautiful area. We are already discussing possible future visits! "

"Easy check-in, excellent communication. Home was very clean with quality furnishings and bedding. Lots of thoughtful touches and extras. Located along Shenandoah River makes it picturesque."

"We appreciate everything from the discrete location,hot tub and many accommodations. What a PERFECT home to stay away from home while we explored the trails and history of the surrounding area. Great eats and trails only minutes away! "

$399 nightly

Aug 14 - Aug 15

Total includes taxes and fees

"The house is well maintained and furnished, and the outdoor space is lovely. We had a great weekend in Leesburg and would come again. "

$324 nightly

Aug 11 - Aug 12

Total includes taxes and fees

"This was a perfect location for our stay. "

"Beautiful property and grounds. Setting was quiet and peaceful. Would stay again."

"Great place to stay on a nice mountain my family and dogs loved itMike was great and answered any questions we had will definitely book again in the future"

"Very comfortable and spacious place with all the comforts of home. We wanted to get away and just relax for a few days and this was perfect!"

"We had a great time! The house overlooks the river and we loved the hot tub and fire pit! "

$366 nightly

Aug 21 - Aug 22

Total includes taxes and fees

"The home is super clean and well maintained! "

"WE HAD A NICE WEEKEND AT THE HOUSE .THE KITCHEN UTENSILS HAS SEEN BETTER DAYS. FYI THE HOUSE IS RIGHT N3XT TL A BUSY ROAD.WE ENJOYED THE HOTTUB AND TV COUCH AREA. THE QINERY NEXT DOOR WAS REALLY NICE"

"Great find for a girls trip…house is close to lots of different activities and very easy to get to. Perfect place to a weekend getaway!"

$372 nightly

Aug 13 - Aug 14

Total includes taxes and fees

"Communication with the host was excellent and an early check in was incredibly helpful - the house served its purpose exactly as expected - hosting friends for the weekend with easy access to the countryside of VA."

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Top Upperville Hotel Reviews

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent

"This is a pretty new property and was a pleasant surprise. Pet-friendly, but not overrun, the room was nice, quiet, and well laid-out. Staff were friendly and helpful, and the common areas very inviting. "