As a business traveler, I've dealt with flight delays, cancellations, missed connections, overbooked rooms, missing reservations but I've never shown up in a city and forgotten to book a hotel. I can see how this is frustrating but this is a thing in anal about. I make sure that I always have a place to sleep and will double and triple check that my reservation exists. Our president obviously forgot to download TripIt on his Samsung Galaxy because had he done so, he would have gotten a message stating that he's missing accommodations for one of the nights.
You just have to love the thought of this administration who thought sending Jared Kushner to the Middle East would solve a problem that has perplexed the region for a thousand years, yet they cannot do something as simple as book a hotel on Expedia.