Where did thieves in Medieval Times sleep?

Answer 1

Jesters were servants, who were paid to entertain. Their work included anything that might be entertaining, ranging from juggling to insulting their lords and their guests at the dinner table.

There were not very many people who were wealthy enough to have servants devoted to making fun in such ways, so jesters were usually servants of wealthy lords. As such they might have slept in the manor itself, as other servants often did. If they did not sleep in the manor, they would have lived nearby, probably in a cottage.

Answer 2

The sleeping habits of thieves throughout the medieval period are well documented, as far as Northern European populations are concerned. There is less information, however, concerning thieves elsewhere (In Persia and East Asia, for example).

The general rule of thumb when thinking about this is as follows: sleeping local correlated directly with the level of the thieves skill and items that they plundered. So, for example, a thief that stole things like bread and onions would generally sleep in a bog or hollowed out tree stump. A thief that stole things like spades or trinkets would sleep in a small village in the Thieves' Forest. And a thief that stole things like a fair maiden's virginity would generally be hanged before they had a chance to sleep.