Replying to Summer road trips

I search barred/ googled the fuck out of this topic but if you know of any applicable threads +k to you. I live 20 mins out of San Fran and would prefer to stay somewhat close to home (no farther east than CO). I am thinking about going for about no more than three weeks (Cheaply). My first thought was to drive to mt. hood and stay with my cousin in Portland and drive up to timberline and ski there  as well as to try and find a cheap place to stay. Any NS with road-trip experience and helpful advice/ ideas for my trip!

Thanks for the help

I re-watched the first season  of tc today which gave me the idea to travel.