Last summer was our first family trip. There were 7 of us all together, and it was the first visit for our DD13, and DS4. We stayed at VWL for six nights / seven days, on the dining plan, and paid rack rate (ugh). We drove from New York over the course of three days. With the extra hotel nights on the way down, and back, gas, food, souvenirs, etc. the grand total came to right around 9,000.
This summer it will be four (or five) of us, we'll be staying at POR for 13 nights / 12 days, with 10 day park tickets. We're hoping to get free dining, and our cost will of course depend a good bit on whether we get it or not. The cost of the room / tickets, assuming that there are five of us, will be $3,400. Gas will be right around $200, unless the price goes way up again. Our hotel on the way down / back will be about $200 also. We figure around $100 for food during the drive, so we're looking at just shy of $4,000 for everything but food / tip on site, and what ever we spend on souvenirs / entertainment while we are there. Probably under $6,000 for five people, 12 days. A much better deal than last year. Of course, if we don't get the free dining, then it will be more like $7,700, but that's still better than last year.