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Worst for me was an old hotel in San Francisco that had so many cockroaches that I didn't unpack anything. The room was strangely clean but I found out in a hurry why the rates were so cheap.
I remember another one. When I was 18, I was dating a guy who went to the Naval Academy in Annapolis. I went to see him for the weekend of his birthday with his sister, and we stayed at a place called the Americana. It was full of roaches. His sister took a few to the front desk and they accused her of bringing them in from home when she asked for a refund! Needless to say, we were not amused. We moved rather quickly!