From here, my first reaction to your post is that you're being (understandably so) wrapped up and dragged along with him in all his indecision and angst. I know you're torn up and feel beaten down and worry about the right mix of detachment from and supportiveness for your H. But you already know he has to do this in his own head.
Would it be possible for you to let go of the vacation issue and maybe go do something alone with your son?
Detach sweetie. So much easier said than done, but you can do hard things.