How To Copy DVDs to iPod using free software for Windows
You'll need two programs, DVD Decrypter and Videora iPod Converter.
Now, use this step by step tutorial for converting DVDs with DVD Decrypter. Note: Once you reach the part about PSP Video 9, stop watching and use the 'One Click Transcode' option in Videora to select and convert the VOB file that DVD Decrypter produces.
Once you have a converted file, add it to iTunes in the same way as music (drag it into the iTunes library) and it will automatically copy across to your iPod.