My potted dwarf pomegranate started flowering a few days ago..
I'm wondering if the flowers will need to be hand polinated since it is so late in the year?? What are the chances it will hold the fruit over winter inside?

Here in Southern California, I don't experience frost. Having said that, my medium sized, in-ground, pomegranate tree loses all its leaves during winter. I have a small potted pomegranate kept outside, and it has a late flower. I doubt it will keep the fruit even if pollinated.

If you keep your tree inside, it might be different though. It may keep the fruit if pollinated.