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Compare 10 Guest Houses in Upperville with updated reviews, rates, and availability.

"The room was so charming and cozy. really nice linens and very comfortable bed. The Inn Keeper, Dan, was fun and knew a lot about the area. Dan is also a great breakfast chef! "

AED 1,497 total

includes taxes & fees

9 Jun - 10 Jun

"We had a fantastic time. Everything was lovely. Thank you!"

"This was a great place to escape to! Very quiet and peaceful but close to some great restaurants and vineyards."

AED 1,573 total

includes taxes & fees

4 Jun - 5 Jun

"Great property, conveniently located to attractions. Host was extremely responsive and friendly. Home and surrounding property was immaculate. We will be staying here again when back in the area. "

"Going to visit Luray caverns and the Shenandoah mountains while out at this beautiful tiny home was amazing for the weekend."

"Winchester was such a lovely town with so many things to do and see. We enjoyed coming home to the cottage each night with its screened-in patio and relaxing view of flowers and shade trees. The cottage was cozy and clean with plenty of linens and staples. I would stay here again, the location was excellent."

"Beautiful Guest House well appointed on beautiful acreage. Would encourage everyone to visit. Host was very helpful and accommodating. You will enjoy the stay ! "