Old Waterstreet is THE perfect bed and breakfast. Lovely town and location; beautifully and comfortably decorated, perfect sized rooms, delicious breakfast and Jeannie is a great host. Great town to stop over and stroll thru . . . . When in town, a visit to the library is a must! More

The location is great and the house was quite nice. We stayed in the cottage suite (top floor...many stairs) which was nice because it had a sitting room included. One caution on the bathroom...I'm tall and the ceiling slopes down so you have to stand close to the shower head or your head will hit the ceiling. I would suggest... More

I had a rare window of opportunity to take a day off and get away for a long weekend, so called and was fortunate to get their last room available! Easy to find, with its own parking, in old town Wincester, within a few blocks of several museums, a very nice local library, and lots of restaurants along a pedestrian... More

My wife and I stayed here for a few nights right after we were married, and I can't say enough great things about this place. Jeannie and Erik were both fantastic and since my wife and I are wine lovers, we got great recommendations for which wineries to go to. Dinner reservations were booked for us, and the place was... More

A traditional B&B, owner-operated, with comfortable yet gracious rooms and public areas. The owner was very knowledgeable and helpful. Breakfast was outstanding. Worth a detour if you find yourself in that part of Virginia and nearby West Virginia and Maryland. More

We very much enjoyed another pleasant 3-night stay at the Old Waterstreet Inn. My wife and I felt like just getting away from our daily grind, remembered our 2009 stay, and chose this comfortable Bed&Breakfast in the heart of Winchester. We loved the warm hospitality of Jeannie and her husband and even joined them for hot cider in front of... More

We stayed at the Inn as part of a present from our children. The inn itself was warm and comfortable, as good as any we have stayed at. I cannot say enough about Jeannie. She is a wonderful hostess and her suggestions made our stay in Winchester memorable. More

My husband and I spent one night at the Old Waterstreet Inn on our way back home from a meeting near Washington, DC. My husband surprised me when he announced that he had made a reservation at a B&B in Winchester. (He is a business traveler and a B&B is outside his comfort zone of Hilton Garden Inns etc :)... More

Very pretty place and nicely decorated. That'sa about it on the plus side. Jeannie, the owner and InnKeeper operates the place with the primary objective of minimizing her time servicing the guests. You are sternly asked when you make a reservation to state your arrival time (so that she does not have to wait around for people I guess). Once... More