sharing hotel rooms
In my personal case it would matter exactly who I was with, and which bed they sleep in.
I would sleep in my briefs or fully clothed with the immediate members of my family and with some mixed sex friends while sleeping totally nude with certain other friends and acquiantances.
Unless we are very comfortable with each others presence in such close proximity I wouldn't sleep nude in the same bed with any female friend simply because I think that she would be more hesitant about that condition than I would.
As my "handle" indicates I am a pro clothing optional entity to some degree but I do know when to put other peoples adverse reactions to my nudism before my own.
I'd just take it all off.