I'm sure it's possible. But I'm sure it wouldn't be straightforward. If you've asked this question, you probably aren't familiar with what will the possible difficulties. In short, if you had to ask this, then the project probably isn't worthwhile for you.
I should start by saying that I'm pretty sure the standard license would prohibit you from doing this.
The biggest problem would be activating Mathematica. The activation done each time is machine specific, but if you're booting from USB, maybe that would work.
An alternative is to activate using the license manager, MathLM.
