In my experience good hotels in Tokyo (four stars and above) will turn a blind eye to almost anything in order to avoid embarrassing their guests. I must have walked into the ANA Intercontinental eight or nine times, dressed up, at ten or eleven at night, headed straight for the guest lifts, and out again in the small hours, and no member of staff has ever stopped me, looked at me funny, or questioned me. I've also met other working girls in the lifts on the way in and out.
I can't speak for business hotels such as Tokyuu, though, since I don't tend to get appointments for them.