If you're talking about playing videos straight from the Vimeo site, yes it can, I just checked this personally to make sure. If you have files downloaded and save them into your Drive it seems it will play them as well, although I am not entirely sure what formats it will play and what format Vimeo saves in if you download the videos.
It also seems to be possible to upload your ITunes videos to Google's Google Play Music Manager and play them from any of your Google connected devices. Here is the support article for doing that:
https://support.google.com/chromebook/answer/183107?hl=en