Not really a machine, but very old.
There was a thread on people's oldest tools but can't seem to find it.
Anyway thought the various tool junkies might find this interesting. It's a bow mill cutter. Very much a one trick pony for cutting the ends on bows for pocket watches etc. The reamers are sized to match each size of end, and are used to accurately ream out the holes in the sides of the pendant. Probably mid 19th century ot thereabouts. Needs some tlc, but very unusual to find one so complete.
The brass tube contains a spring which holds the end of the bow against the cutting head, turning the handle then drives the cutter to machine the end.