This doesn't do cygwin ssh yet, as I'm trying to do this via a new (as of yet unwritten) vagrant winrm provisioner. However these boxes are up enough to 'knife bootstrap windows winrm'
added windows 2008, 2008r2, and 7 with winrm support
Does your winrm piece work with domain controllers? Or is it using local accounts on the windows box? I haven't had luck with 'knife bootstrap windows winrm' when the VM is joined to a domain.
nm, i just found this:
winrm=WinRM::WinRMWebService.new(endpoint, :plaintext, :user => 'Administrator', :pass => 'vagrant', :basic_auth_only => true)