Look at the Size of It!

That's what she said.

When you first loot a pillow, a timer starts. After a few minutes a group of sleepy dark iron workers spawn. A few minutes later, a second group spawns. A few minutes after that, the chambermaid spawns. Of course, by this time most players have long since turned in the quest and moved on.

Deleting and re-looting pillows is not necessary -- the only thing it accomplishes is keeping you in the area while the timer continues to run.

If you, like me, haven't completed this quest for whatever reason:
-Go to Searing Gorge
-49.9, 46.1 enter the cave
-Go straight, keeping to your right, then take the 1st right; the tunnel should now look like where the dwarves rest, with bedrolls and stuff. Aside from regular mobs, this is where the maid spawns.
-If she's not spawned, check the other comments here that talk about it. Once you kill her, she physically drops a blue, square pillow. Just click on it to get the quest.
-Go outside the quest to Thorium Point to deliver quest.

Hope this helps.