Thanks for the clarification . Since you do know him / his background, and you have been on a few casual dates, I'd say that you are ready for "the next step". I'd go with the weekend away - life is too short for wasting time with further dates as if you were an innocent teenager.
Tell him that you are worried about rushing into something you are not ready for - I'm sure that since you already know him well, he'll be understanding about the sex part of things. Ask for separate rooms, and if things work out you can change the arrangement. Best wishes to you !