Well, it really does depend on the income of the house, which in turn is driven by technology, centralization, tax collection, and so on. I should also tag @racefortheironthrone on this one.
We can chart a course though. Around 1300, smaller English knights would have approximately 5 people in their retinue, more powerful bannerets would have 13-15, judging by pay records. In the 14th century, this number explodes. In 1322, the average noble had twenty men, in 1341, it was thirty in Scotland. By 1359 a banneret commanded on average sixty men. but Henry Grosmont, the incredibly wealthy Duke of Lancaster, had over a thousand. By 1380 the Earl of Buckingham brought 2,500 men.
Thanks for the question, Terra.
SomethingLikeALawyer, Hand of the King
In addition to the factors above, it also depends on whether one’s military forces are organized through strict or bastard feudalism – in other words, are you bounded by how many knight’s fees your fief contains, or can you make up the difference with cash?