I’d be leery of boarding a cat because they do get so very upset about changes in the environment and because kennels tend to be noisy places, which would freak my cats right out. I’ve had good experiences with pet sitters, both professional and not-so-professional. We’ve had three types:
Twice we’ve been lucky enough to have a neighbor who’ll come over daily (or twice-daily, because she’s just that nice) to feed and play with and love on the animals for free in exchange for us being willing to do the same for her animals. I’d be uncomfortable asking her to administer medication, though, and if you don’t have a neighbor like this handy, you can’t really go out and get one.
We’ve also had teenaged daughters with reliable friends who welcome the chance to make some extra money, and we’ve hired them to stay over as live-in pet-sitters while we’re gone. This has worked out splendidly for us, but you really, really, really have to choose your teens wisely, and there’s a relatively small window between the time a teenager is old enough to be independent and drive herself to and from the house and the time that she goes off to college and/or gets a real job, making her unavailable. Our candidates have dwindled away to one or two because of this.
We’ve hired two different professional pet-sitters who were recommended by our vet or by someone in the vet’s office. They have both worked out well, but they typically will only come once a day, and they usually don’t have the time to sit around and spend quality time with the pets. They are, however, much more qualified to give medication, and when we’ve had to leave a pet who had medical needs, we’ve called on them. They are pretty expensive (I believe it started at $20 a day the last time we used one), but they came over once or twice beforehand to meet the pets and get a feel for how their routine went. They were also experienced in pilling cats, and I trusted them to know when they should call a vet if something came up.