Basic Molnija based pocket watches can be found on eBay for under $30; they're good, rugged watches, but most of the cases range from gaudy to ridiculous. Molnija's from the 50's and 60's have nicely decorated movements and plain, functional cases, but are usually worth more. They're based on an old Cortebert design (the same design used for Rolex pocket watches in the 30's and 40's); the Russians bought their equipment from Cortebert in the first place.
When looking at vintage pocket watches, don't forget to factor in the cost of getting the watch serviced. Depending on where you are, that'll cost you anywhere from $50 to $150. And you won't find many that are skeleton-style. Chances are that anything you find that's vintage skeleton is newer or fake.