Tolkien himself described Bombadil as an enigma. There are many threads here that debate who or what he was, but if you start reading them you may end up even more confused than you are now.
As for the dreams, I believe they all dreamed of Isengard. Frodo's dream was of Gandalf stranded atop Orthanc, that was plain. Pippin dreamed of "branches fretting in the wind, twig-fingers scraping wall and window" an image similar to the description of the Ents tearing at the walls of Isengard. Merry's dream was of the sound of water falling "then spreading, spreading irresistibly all round the house into a dark shoreless pool." Very much what the Ents did to Isengard to clean it up after they conquered it. Sam was not at the conquest of Isengard and had no dream at all.
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Yet all the while I sit and think of times there were before,
I listen for returning feet and voices at the door.
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