Vamos perguntar o próprio homem (Chester Ramey):
E10) Why does 'cd //' leave $PWD as '//'?
POSIX.2, in its description of 'cd', says that three or more leading slashes may be replaced with a single slash when canonicalizing the current working directory.
This is, I presume, for historical compatibility. Certain versions of Unix, and early network file systems, used paths of the form //hostname/path to access 'path' on server 'hostname'.