diff --git a/lib/vagrant/util/platform.rb b/lib/vagrant/util/platform.rb
index a55c4f61c..c3b16d083 100644
--- a/lib/vagrant/util/platform.rb
+++ b/lib/vagrant/util/platform.rb
@@ -14,6 +14,10 @@ module Vagrant
           platform.include?("darwin9")
         end
 
+        def cygwin?
+          platform.include?("cygwin")
+        end
+
         [:darwin, :bsd, :freebsd, :linux, :solaris].each do |type|
           define_method("#{type}?") do
             platform.include?(type.to_s)
diff --git a/plugins/providers/virtualbox/action/import.rb b/plugins/providers/virtualbox/action/import.rb
index 14ac2b0bb..0dfd52f89 100644
--- a/plugins/providers/virtualbox/action/import.rb
+++ b/plugins/providers/virtualbox/action/import.rb
@@ -12,6 +12,9 @@ module VagrantPlugins
 
           # Import the virtual machine
           ovf_file = env[:machine].box.directory.join("box.ovf").to_s
+          if Vagrant::Util::Platform.cygwin?
+            ovf_file = `cygpath -m '#{ovf_file}'`.chomp
+          end
           env[:machine].id = env[:machine].provider.driver.import(ovf_file) do |progress|
             env[:ui].clear_line
             env[:ui].report_progress(progress, 100, false)
diff --git a/plugins/providers/virtualbox/driver/base.rb b/plugins/providers/virtualbox/driver/base.rb
index 5dfb23aa5..e7cc2e035 100644
--- a/plugins/providers/virtualbox/driver/base.rb
+++ b/plugins/providers/virtualbox/driver/base.rb
@@ -25,7 +25,7 @@ module VagrantPlugins
           # Set the path to VBoxManage
           @vboxmanage_path = "VBoxManage"
 
-          if Vagrant::Util::Platform.windows?
+          if Vagrant::Util::Platform.windows? || Vagrant::Util::Platform.cygwin?
             @logger.debug("Windows. Trying VBOX_INSTALL_PATH for VBoxManage")
 
             # On Windows, we use the VBOX_INSTALL_PATH environmental
@@ -33,6 +33,9 @@ module VagrantPlugins
             if ENV.has_key?("VBOX_INSTALL_PATH")
               # Get the path.
               path = ENV["VBOX_INSTALL_PATH"]
+              if Vagrant::Util::Platform.cygwin?
+                path = `cygpath -u '#{path}'`.chomp
+              end
               @logger.debug("VBOX_INSTALL_PATH value: #{path}")
 
               # There can actually be multiple paths in here, so we need to