Add multiple images to a page sidebar

What I am trying to achieve is this:

I have a simple page and I want to dynamically add multiple images to it on the sidebar one underneath another. I was thinking about either using meta boxes, post thumbnail or custom field. I am looking for a nice and simple method to do that.

Here is a screenshot that better explain what I am looking for:

http://bit.ly/y4Vi19

Notice that adding images to the post itself must be differ than add images to the sidebar.

any help will be appreciated

Thanks, Gil

I would recommend using MetaBoxes.

A nice tutorial is here: http://www.farinspace.com/wpalchemy-metabox/