48Rob
There were some trailers produced, in the 30's at least, that were covered in leatherette (early vinyl)
http://www.rvmhhalloffame.org/newimages ... 0wagon.jpg
That's really something. Imagine, though it'd be hard to replicate the patina, a teardrop covered in that faded burgundy "leatherette". I think it'd be fantastic-looking.
I second Rob's post. While looking through the Vintage Plans link at the top of the page, one of the two '30s-era teardrop plans said it was covered in leatherette. If said covering was impermable to/by water, then... I'm still pondering covering my tear this way.

And to reply to the OP's question, yes; the side of that trailer looks to be padded.
The chairs were simply wooden folding chairs of the day, a style still used in the picture business.
