Search Vacation Homes in Upperville

"Little Oatlands was the perfect place for our outdoor wedding and we’re very happy we chose it. If you are planning to do the same, and have family stay in the guest house for the weekend, read the contract *carefully*. We skimmed it and failed to realize that you’ll need to take all trash bags to the dumpster by the barn and strip all of the bed sheets and put them downstairs, etc…"

"Everything was fine."

"Loved the view, the pool, brewery and the 3 floors of spaces to sleep worked perfect for our group."

"We had a good time at the place. The big kitchen table is perfect for gathering when the weather keeps you from the fabulous fire pit. We would go back if we had an occasion to."

"We had a great stay! Thank you!"

"Proximity to RMA campus worked perfectly for our extended family attending graduation ceremonies and celebrations."

"We were in town for the comedy show at the casino. House was within walking distance however not a walk you would want to take wearing heels. Very quiet neighborhood with plenty of restaurants close by. The house was very clean and comfortable beds. Had a really great time!! Thank you!!!"

"This was a beautiful home for a 30 something Bachelorette Weekend. The proximity to the tasting room was convenient and the grounds were beautiful. Our groups had an excellent time and hope to be back!"

"We had such a lovely time in Virginia. This property was so clean and well appointed. We also enjoyed the location right next to the W&OD trail."

"There were 9 adults and 1 baby in our group and the property worked out great for us. The owners had great communication and everything about the home came as advertised. Plenty of room, very clean, and some nice extra touches. We recommend and would stay here again."

"We were a group of 10 people with 2 infants and absolutely enjoyed our stay. The location is amazing, nestled in the woods with deers and birds visiting the property. The house had everything we needed from linens to towels to utensils and toiletries. The listing says 4 bedrooms, but the bunk bed area in the basement can also be considered an additonal room. Would definitely recommend this place when visiting Virginia/Shenandoah NP."

"We enjoyed the location of this quiet highland home away. It was close enough to amenities and sites, but far enough to feel like we were staying in the country. We were able to do day trips to Harpers Ferry, Winchester, Leesburg, Middleburg, but also just enjoyed this surroundings at the property. There were plenty of bed options and the kitchen was well-maintained and equipped. We will return."

"Great for lots of family and friends so everyone is together and not hotel room or hotel lobby hopping"

"The house was newly renovated, clean, well stocked and spacious. My husband and I spent a long weekend hiking and enjoying the change of the season."

"John was super helpful and the place was lovely."

"The location was minutes from Skyline Drive and we were close to tons of hiking. Front and back yard were both fenced and great for my niece and my dogs. House was super clean and had everything we needed. Only suggestion is a bigger couch or more seating in the living room. It was a little tight trying to relax at night in front of the TV."

"The house was perfect… close to everything, very clean. Plenty of space and a great Kitchen. With family near by this house made it very easy for us to visit and enjoy our time with them over Easter. We will be staying here again."

"We were traveling to the area for an AKC event, and stayed for three nights prior to Thanksgiving. Matt's house was the perfect home base location! Loved the moutain setting while still being convenient to the places we need to travel to. House was beautiful and clean, and we loved watching the deer roam the property. Second time staying at one of Matt's properties, and neither disappointed!"

"We stayed at Loving Gallery & Studio last weekend with a group of 15 for our Mothers 90th Birthday The home is just beautiful and well laid out for large groups. There are 6 beautiful bedrooms plus sofa beds and all the possible amenities! Lots of wood for stoves, fireplaces & firepit, bathroom amenities, bottled water in each room, well stocked kitchen with spices and everything you could possibly need for cooking in your home away from home. There are also several beautiful outdoor spaces to...