I have mostly worked for small companies, without a lot of travel. However, I worked for one small CPA firm where my boss and I were attending an out-of-town IRS conference together. We shared a room, and it was very awkward. I let her know ahead of time that I sometimes snore, and I brought my own earplugs because I'm a very light sleeper. I normally sleep au naturel, so I had to buy a new nightie (which I don't think I've used since). There was also no alone time during the three-day conference - meals, evenings, were all with her. Luckily, during the conference itself we signed up for different courses going at the same time, so I got some escape.
She is a very 'proper' lady, so I constantly felt unwashed and sloppy in her presence.