When you turned on vacation time, was it your turn to move in any of your games?
Vacation Didn't Work
yes 
For basic members, you have to have made a move in all of your games before activating the vacation setting.
... I then clicked OK to both of the popup indicators confirming that I was on vacation. ...
Try it again, if the popup indicators you saw were confirmations rather than warning messages you could submit a bug report.
http://support.chess.com/Tickets/Submit
So I left for the weekend and was going to be gone for 3 days. I knew I wasn't going to get to a computer during that time so I put on my vacation settings. I wrote a message along the lines of "gone for the weekend, sorry, be back soon." I then clicked OK to both of the popup indicators confirming that I was on vacation. I came back and LO AND BEHOLD 70+ losses on time. Is there anyway to rectify this wrong? Did the system not accept it? What happened?