Is there an rsync-like mode for WinSCP (or a similar tool)?
Use Synchronize (Ctrl-S):
The prompts afterwards walk you through what you need to do.
There is cwRsync which I use for backing up data from Windows PCs to Linux servers.
Older versions are available without fee
As per @warren's answer, WinSCP can synchronize files.
If you want to do it periodically, you need to script it (WinSCP supports scripting) and schedule the WinSCP script using the Windows Scheduler.