The Hotel Pennsylvania in Midtown Manhattan comes to mind - I was booked there as part of a concert performance at Carnegie Hall by my choir. I assert, to this day, that the fact that this property has "hotel" in its title is false advertising. Ratty room, nonfunctional air conditioning (94 degrees at 11 p.m. - I love New York summers) slow elevators, nonexistent front desk, and, the best, a "concierge" who recommended Sbarro as a good place for an Italian meal.
Perhaps Dave Barry summed it up best...
http://www.miami.com/mld/miamiherald...ry/3375167.htm