diff --git a/CHANGELOG.md b/CHANGELOG.md
index aa72900ab..1308ec73e 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,5 +1,6 @@
 ## 0.7.0.beta2 (unreleased)
 
+  - Puppet server provisioner. [GH-262]
   - Use numeric uid/gid in mounting shared folders to increase portability. [GH-252]
   - HTTP downloading follows redirects. [GH-163]
   - Downloaders have clearer output to note what they're doing.
@@ -9,7 +10,7 @@
   - `config.ssh.forward_x11` to enable the ForwardX11 SSH option. [GH-255]
   - Vagrant source now has a `contrib` directory where contributions of miscellaneous
     addons for Vagrant will be added.
-  - Puppet server provisioner. [GH-262]
+  - Vagrantfiles are now loaded only once (instead of 4+ times) [GH-238]
 
 ## 0.7.0.beta (December 24, 2010)
 
diff --git a/lib/vagrant/config.rb b/lib/vagrant/config.rb
index 88be0d2f7..354eb60c8 100644
--- a/lib/vagrant/config.rb
+++ b/lib/vagrant/config.rb
@@ -32,6 +32,7 @@ module Vagrant
   class Config
     # An array of symbols specifying the load order for the procs.
     attr_accessor :load_order
+    attr_reader :procs
 
     # This is the method which is called by all Vagrantfiles to configure Vagrant.
     # This method expects a block which accepts a single argument representing
@@ -55,15 +56,22 @@ module Vagrant
       value
     end
 
-    def initialize
+    def initialize(parent=nil)
       @procs = {}
       @load_order = []
+
+      if parent
+        # Shallow copy the procs and load order from parent if given
+        @procs = parent.procs.dup
+        @load_order = parent.load_order.dup
+      end
     end
 
     # Adds a Vagrantfile to be loaded to the queue of config procs. Note
     # that this causes the Vagrantfile file to be loaded at this point,
     # and it will never be loaded again.
     def set(key, path)
+      return if @procs.has_key?(key)
       @procs[key] = [path].flatten.map(&method(:proc_for))
     end
 
diff --git a/lib/vagrant/environment.rb b/lib/vagrant/environment.rb
index 7339775b1..73bc26cf8 100644
--- a/lib/vagrant/environment.rb
+++ b/lib/vagrant/environment.rb
@@ -23,6 +23,9 @@ module Vagrant
     # The {UI} object to communicate with the outside world.
     attr_writer :ui
 
+    # The {Config} object representing the Vagrantfile loader
+    attr_reader :config_loader
+
     #---------------------------------------------------------------
     # Class Methods
     #---------------------------------------------------------------
@@ -308,6 +311,7 @@ module Vagrant
     # Reloads the configuration of this environment.
     def reload_config!
       @config = nil
+      @config_loader = nil
       load_config!
       self
     end
@@ -320,23 +324,23 @@ module Vagrant
       first_run = @config.nil?
 
       # First load the initial, non config-dependent Vagrantfiles
-      loader = Config.new
-      loader.load_order = [:default, :box, :home, :root, :sub_vm]
-      loader.set(:default, File.expand_path("config/default.rb", Vagrant.source_root))
-      loader.set(:box, File.join(box.directory, ROOTFILE_NAME)) if !first_run && box
-      loader.set(:home, File.join(home_path, ROOTFILE_NAME)) if !first_run && home_path
-      loader.set(:root, File.join(root_path, ROOTFILE_NAME)) if root_path
+      @config_loader ||= Config.new(parent ? parent.config_loader : nil)
+      @config_loader.load_order = [:default, :box, :home, :root, :sub_vm]
+      @config_loader.set(:default, File.expand_path("config/default.rb", Vagrant.source_root))
+      @config_loader.set(:box, File.join(box.directory, ROOTFILE_NAME)) if !first_run && vm && box
+      @config_loader.set(:home, File.join(home_path, ROOTFILE_NAME)) if !first_run && home_path
+      @config_loader.set(:root, File.join(root_path, ROOTFILE_NAME)) if root_path
 
       # If this environment is representing a sub-VM, then we push that
       # proc on as the last configuration.
       if vm
         subvm = parent.config.vm.defined_vms[vm.name]
-        loader.set(:sub_vm, subvm.proc_stack) if subvm
+        @config_loader.set(:sub_vm, subvm.proc_stack) if subvm
       end
 
       # Execute the configuration stack and store the result as the final
       # value in the config ivar.
-      @config = loader.load(self)
+      @config = @config_loader.load(self)
 
       # (re)load the logger
       @logger = nil
diff --git a/test/vagrant/config_test.rb b/test/vagrant/config_test.rb
index 985639ee6..0db26b8e8 100644
--- a/test/vagrant/config_test.rb
+++ b/test/vagrant/config_test.rb
@@ -62,6 +62,17 @@ class ConfigTest < Test::Unit::TestCase
       assert_nothing_raised { @instance.load(nil) }
     end
 
+    should "not reload a file" do
+      foo_path = vagrant_box("foo").join("Vagrantfile")
+
+      vagrantfile(vagrant_box("foo"))
+      @instance.set(:foo, foo_path)
+
+      # Nothing should be raised in this case because the file isn't reloaded
+      vagrantfile(vagrant_box("foo"), "^%&8318")
+      assert_nothing_raised { @instance.set(:foo, foo_path) }
+    end
+
     should "raise an exception if there is a syntax error in a file" do
       vagrantfile(vagrant_box("foo"), "^%&8318")
 
diff --git a/test/vagrant/environment_test.rb b/test/vagrant/environment_test.rb
index a6cd69ac7..2810a6e3b 100644
--- a/test/vagrant/environment_test.rb
+++ b/test/vagrant/environment_test.rb
@@ -393,7 +393,7 @@ class EnvironmentTest < Test::Unit::TestCase
         create_box_vagrantfile
         vagrantfile(@env.root_path, "config.vm.box = 'box'")
 
-        assert_equal "box.box", @env.config.package.name
+        assert_equal "box.box", @env.primary_vm.env.config.package.name
       end
 
       should "load from home path if exists" do