We stayed at Bessho in April this year. We went there from Matsumoto by car, and stopped at the Daio wasabi farm on the way. We splurged, and stayed in an expensive room here:
http://hanaya.naganoken.jp/ , but there are also rooms in the main building at quite reasonable prices which look lovely.
The ryokan itself is BEAUTIFUL, serene, with wonderful service, food, and bathing, and set in lovely gardens. It's unusual in that it's in a "Taisho Modern" architectural style (if you look at the pictures, you'll see what they mean much better than if I try to explain it).
It was so restful and lovely in the ryokan that we didn't go out to explore the town after checking in, but we did spend two or three hours beforehand looking around the various shrines (very nice), having lunch (hard to find on a weekday at the beginning of April - there were very few people around and lots of places were closed), and stopping for a coffee in a fantastic café & gelateria with a "hidden" back room with a charming owner and where you pick your own cup from a selection in a case on the wall. It turned into a wine bar in the evening, apparently, and I think it would be lovely place to go after dinner.
We saw a couple of public bathhouses as we walked around; they looked nice but we didn't go in them (only because we were limited for time - we wanted to check into the ryokan as soon as we could, and we also wanted to see the various temples/shrines).
The only thing I'd say - looking at what you say you want - is that it was really quiet. It was a rainy weekday at the beginning of April, and we didn't go out into the town in the evening, so perhaps our experience wasn't typical, but we scarcely saw another person. That may be a good thing or a bad thing for you, but I just wanted to tell you.