diff --git a/lib/vagrant/bundler.rb b/lib/vagrant/bundler.rb
index 28ec66674..6124eb181 100644
--- a/lib/vagrant/bundler.rb
+++ b/lib/vagrant/bundler.rb
@@ -40,6 +40,20 @@ module Vagrant
     def initialize
       @plugin_gem_path = Vagrant.user_data_path.join("gems", RUBY_VERSION).freeze
       @logger = Log4r::Logger.new("vagrant::bundler")
+
+      # TODO: Remove fix when https://github.com/rubygems/rubygems/pull/2735
+      # gets merged and released
+      #
+      # Because of a rubygems bug, we need to set the gemrc file path
+      # through this method rather than relying on the environment varible
+      # GEMRC. On windows, that path gets split on `:`: and `;`, which means
+      # the drive letter gets treated as its own path. If that path exists locally,
+      # (like having a random folder called `c` where the library was invoked),
+      # it fails thinking the folder `c` is a gemrc file.
+      gemrc_val = ENV["GEMRC"]
+      ENV["GEMRC"] = ""
+      Gem.configuration = Gem::ConfigFile.new(["--config-file", gemrc_val])
+      ENV["GEMRC"] = gemrc_val
     end
 
     # Enable Vagrant environment specific plugins at given data path
diff --git a/test/unit/vagrant/bundler_test.rb b/test/unit/vagrant/bundler_test.rb
index 4428be470..99fe9d0cd 100644
--- a/test/unit/vagrant/bundler_test.rb
+++ b/test/unit/vagrant/bundler_test.rb
@@ -28,6 +28,19 @@ describe Vagrant::Bundler do
     expect(subject.env_plugin_gem_path).to be_nil
   end
 
+  describe "#initialize" do
+    let(:gemrc_location) { "C:\\My\\Config\\File" }
+
+    it "should set up GEMRC through a flag instead of GEMRC" do
+      allow(ENV).to receive(:[]).with("VAGRANT_HOME")
+      allow(ENV).to receive(:[]).with("USERPROFILE")
+
+      allow(ENV).to receive(:[]).with("GEMRC").and_return(gemrc_location)
+      expect(Gem::ConfigFile).to receive(:new).with(["--config-file", gemrc_location])
+      init_subject = described_class.new
+    end
+  end
+
   describe "#deinit" do
     it "should provide method for backwards compatibility" do
       subject.deinit