The answer is yes.
For a Windows PC you need a decrypter like AnyDVD or DVDFab.
It works best if you rip the contents to your hard drive first and then use a program like Handbrake, they have iPod presets, to change it into a form you can put on your iPod.
I don’t know much about DVDFab so someone else will have to answer your questions about that program.
I use AnyDVD, and then CloneDVD to rip to my hard drive ( 21 day free trial before you buy them so you can try them out first).
Handbrake is free and a great program but there is a CloneDVD Mobile (You can do a straight rip, after decrypting, with either Handbrake or Mobile but not all DVDs are amenable to that.) that also has a 21 day free trial so there’s no reason you can’t try them all and pick the set up that works best for you and fits your budget.