I'm literally cutting and pasting an answer I put out here yesterday to the same kind of question:
He's playing a game, and you're losing! :)
My son did this around that age. We eventually got to the point where he was waking up 3-4x/night and wanting to be rocked back to sleep...because we kept doing it.
Finally, after 1 night of waking every 2hrs, at 17mos, we let him CIO. I remember it VIVIDLY. He cried for 23 minutes. After that, he went back to sleep, and we had no more issues...until we moved him to a toddler bed. Whole new ballgame/different story.
He's crying because you'll come in and he wants to hang out with you. That's all. If he's not sick, then he just wants some company. You'll have to nip this in the bud.
There will be many times where you have to re-sleep train them. I'm doing it again right now for the same kiddo I menitoned above. He's 2.5, now and in his own bed. We're back to having to CIO, since he got used to us laying down with him at bedtime after he was sick.
It sucks to do it, but it works every time.