I'm only guessing but:
Relatively close to a star, like Jupiter or Saturn orbit, probably.
Internal reflections on the windows would likely be problematic, kinda like trying to look out a plane window flying at night. The cabin lights make it pretty hard. But from a pitch black room I reckon it'd be visible.
Pluto orbit, probably not. Dark room and dark adapted, maybe
Interstellar, not likely.
I have nothing to base this on, just guessing as I said.
EDIT:
Actually, I may have just changed my mind..... starlight can be pretty damn bright once dark adapted on a moonless night... but I wonder how much of this is contributed by atmospheric skyglow(airglow) and light scattered by interplanetary dust?