diff --git a/plugins/guests/windows/cap/rsync.rb b/plugins/guests/windows/cap/rsync.rb
index e391b92db..aa9f1bcdf 100644
--- a/plugins/guests/windows/cap/rsync.rb
+++ b/plugins/guests/windows/cap/rsync.rb
@@ -2,8 +2,17 @@ module VagrantPlugins
   module GuestWindows
     module Cap
       class RSync
+        def self.rsync_scrub_guestpath( machine, opts )
+          # Windows guests most often use cygwin-dependent rsync utilities
+          # that expect "/cygdrive/c" instead of "c:" as the path prefix
+          # some vagrant code may pass guest paths with drive-lettered paths here
+          opts[:guestpath].gsub( /^([a-zA-Z]):/, '/cygdrive/\1' )
+        end
+
         def self.rsync_pre(machine, opts)
           machine.communicate.tap do |comm|
+            # rsync does not construct any gaps in the path to the target directory
+            # make sure that all subdirectories are created
             comm.execute("mkdir '#{opts[:guestpath]}'")
           end
         end
diff --git a/plugins/guests/windows/plugin.rb b/plugins/guests/windows/plugin.rb
index 47ca67e3f..d22dc2743 100644
--- a/plugins/guests/windows/plugin.rb
+++ b/plugins/guests/windows/plugin.rb
@@ -64,6 +64,11 @@ module VagrantPlugins
         Cap::MountSharedFolder
       end
 
+      guest_capability(:windows, :rsync_scrub_guestpath) do
+        require_relative "cap/rsync"
+        Cap::RSync
+      end
+
       guest_capability(:windows, :rsync_pre) do
         require_relative "cap/rsync"
         Cap::RSync
diff --git a/plugins/synced_folders/rsync/helper.rb b/plugins/synced_folders/rsync/helper.rb
index 594410436..e155d61f7 100644
--- a/plugins/synced_folders/rsync/helper.rb
+++ b/plugins/synced_folders/rsync/helper.rb
@@ -38,6 +38,11 @@ module VagrantPlugins
         hostpath  = File.expand_path(hostpath, machine.env.root_path)
         hostpath  = Vagrant::Util::Platform.fs_real_path(hostpath).to_s
 
+        # if the guest has a guest path scrubber capability, use it
+        if machine.guest.capability?(:rsync_scrub_guestpath)
+          guestpath = machine.guest.capability(:rsync_scrub_guestpath, opts)
+        end
+
         if Vagrant::Util::Platform.windows?
           # rsync for Windows expects cygwin style paths, always.
           hostpath = Vagrant::Util::Platform.cygwin_path(hostpath)