$42 (including tip) about 3 or 4 times per year with a hairstylist who was another mom at my kids' montessori (she has her own business). I'd like to go more often, as she does a great job and I feel great when she cuts it, but I find it difficult to schedule the time to go. So DH cuts if for me once in a while. He does a pretty good job, but she does a better job. I really should make an appointment now. She is also an amazing colorist, and she's fixed bad hair color on my before. I've stopped coloring it, but if I ever start again, I'll go to her.
DH cuts his own hair and the kids' hair. I used to pay $10-20/cut for the kids, but DH got better at it, so he does it now.