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Windows offers no out-of-the-box rsync utility. By far, the most commonly used external utilities for Windows rsync are built with the GNU Cygwin libraries. The cost for this convenience is that rsync on Windows has to be provided paths that begin “/cygdrive/c” rather than “c:/“ like other Windows-API utilities. Compounding the situation, rsync doesn’t create paths/to/sub/targets and so the vagrant plugin code, when performing an rsync, is responsible for creating intermediate directories in guest paths if there are any. Furthermore, the mkdir utility in Windows is not another Cygwin utility like rsync but the routine mkdir of Windows command.com. Therefore, while rsync needs the /cygwin paths, mkdir uses the Windows paths. Later, the chef_solo.rp provisioner running within the guest will expect to find Windows-style paths in its solo.rb configuration file. Due to all this, vagrant has to keep track of both the original, possibly dirty Windows guest path and the cygwin-scrubbed guest path.
Vagrant Core Plugins
These are plugins that ship with Vagrant. Vagrant core uses its own plugin system to power a lot of the core pieces that ship with Vagrant. Each plugin will have its own README which explains its specific role.