@David-and-Annie0
Yes, always. But usually only once during their stay.
I don't take it personally or hold it against them if I get no response because I do respect their privacy but many thank me for checking on them. I say something along the lines of "Just checking in to make sure you are settling in nicely and that you're comfortable. Let me know if you need anything!" In over 400 reservations, no one has ever told me they needed anything.
I often thought about saying something like "Just checking in blah blah. . . . Please don't feel like you need to respond if all is going well and you're enjoying yourself." That way you are setting the tone for no news is good news.
Another point, if you ever get a bad review about something that you could have easily fixed, you can rebuttal with the fact that you opened all lines of communication and were easy to reach.