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Hey leon,
Depends on which email program you use, however, I use Outlook at work and all I do is highlight the files I want to attach in explorer, copy using CTRL C and then in the BODY of the email I am creating, Paste using CTRL V and then ALL the files I have selected appear in the email as attachments all at once.
Of course, the bigger the files, the longer it takes and the longer it takes to send the email overall. Zipping them is easier, winzip or WinRAR will do this for you, both if which have trial versions or are free.
Give this a go, some email programs wont let you select more than one file at a time....
Cheers
Chris
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