Holiday Homes in Middleburg

"This property was perfect for our family reunion, in conjunction with a wedding in Middleburg. The house was interestingly rambling, and had perfect spaces for everyone who came. The grounds, garden, and swimming pool were cherries on top! It was the perfect setting for a large gathering, with plenty of spaces for different activities and conversations. Such a unique property!"

"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!"

"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!"

"I booked this property for a group to stay for an equestrian event at Frying Pan Park. The house was perfect for our group. ITs well laid out, close to tons of restaurants, and to the venue. We had a blast and I would absolutely stay here again!"

"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 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."

"The property was nice. Unfortunately the house next door caught on fire while we were staying at this property. The house next door was a total loss. Very frightening!"

"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...

"We were a group of 11 friends staying at the house for the Wine Country 10K. The house was amazing. The listing doesn’t even do it justice. Even though it rained on the main day we were there we were still able to hang out in the hot tub and around the bar, because they were covered, and enjoy meals together in the beautiful and well stocked kitchen and dining room. Despite being 11 adults in the house we didn’t feel at all cramped. There was a small issue in the morning while we were there, but...

"We absolutely loved this house. The location was so perfect and overlooks the river. Can be enjoyed in all seasons but the pool will be amazing in the summer. We enjoyed the wineries but struggled to get Ubers around town. All of the wineries and breweries have beautiful views as well. Great for a friends weekend !"