MSDN has this to say about the Round() function in VBA:
Although the Round function is useful for returning a number with a specified number of decimal places, you cannot always predict how it will round when the rounding digit is a 5. How VBA rounds a number depends on the internal binary representation of that number.
It does not say the same thing about VBScript, but I venture to guess that the same thing is going on.
Bottom line is, if you want a Round() function that will actually behave predictably, you'll have to write your own. :/
(If you want a function that does "normal" rounding, not some fancy-shmancy "round to even" formula, use FormatNumber(). As far as I know, that one actually behaves predictably, i.e. x.5 will always round up.)