We used orbitz to reserve our room late on a week night. We had no problems getting in and the front desk staff was very helpful and efficient. The public areas are clean and nice. Some of the furniture in The Half Note lounge were worn and looked a little old, but were comfortable.
The room was small, but lovely. Our king size bed was fairly comfortable, but the pillows, sheets, and blankets, were not near the quality of the ones at the Best Western Plus we stayed at a month ago. The bathroom looked nice, but the door didn't seal well and the floor outside got extremely wet. Overall, it was fine, and we enjoyed our room, but I wasn't "wowed" for one of the best hotels in Winchester.
I think we'll plan ahead a little more next time and stay at a bed & breakfast if we need to get away for a night.
Oh, the only breakfast available was at The Dancing Goat. Hot chocolate was $5 but the rest of the food was decently priced. We didn't eat there though. They had coffee and tea available in the lobby and a gift shop with candy and soda.
It definitely felt nicer upon entry than a Holiday Inn, but I'd say you get a better value at a nice new Holiday Inn etc.