There is no reason why a lady shouldn't express she has feelings to a man. You are in the best position to read the situation. You must have noted his interest at enjoying your company. Tell him you are considering taking a short break, would be nice if you knew a place he liked, ask him would he like to join you ?

Always read his body language and eye contact, they are dead give aways in a man.

Good luck with it.
Divis.