In all my travels around North America, I've slept in all kinds of interesting places... old barns, abandoned houses, caves, beaches, etc, but this had to be the most unique on-the-road lodging experience I've ever had.
Last month I took a hitching trip around Shikoku Island in Japan. One evening when I had just arrived in Kochi city I took a local bus out to the coast. I was planning to sleep on the beach when I spotted this old hotel with broken out windows and a fence around it. It appeared to have been abandoned for several years. As soon as it got dark, I went to investigate. With a scramble up a rock and a gap in the fence it was surprisingly easy to get in. I used my flashlight and explored several rooms. They were all trashed and smelled like mold but I couldn't resist this opportunity. I "checked myself in" to one of the top floor suites, and put my tarp down over the old dusty mattress and had a good sleep with the sound of the waves crashing below outside. I never did find out the story on that hotel, but it must have been a product of the economy boom in the '90s and the subsequent recession. I put up some pictures of it here. You gotta see this place:
http://www.h5.dion.ne.jp/%7Ejmurray/oth ... /hotel.htm
What are some of the more interesting places you've crashed for the night?