On your vista machine, open Google docs (https://docs.google.com
), click 'Upload', then either 'File' or 'Folder' as is your want.
Your documents will then be uploaded to the cloud and converted* into Google docs format, which then means you can access them from the Chromebook, your Vista PC, or anywhere else just by signing into Google Docs.
Stop thinking about 'transferring things to my chromebook' and instead start thinking 'put my things on the web'
Your chromebook is just a web browser, and it doesn't work with local files well.
*Google Docs will convert what it can, it might struggle with some file formats. If this is the case open them up in Works and 'Save As' to something else - .doc should be fine.