While I am frugal I have not thought of this before and one thing I do try to do is have fun.
So, if you want to be stuck in a stuffy Hotel in downtown San Francisco, by all means have fun.
If you want to save money, get to see the backbone of Silicon Valley and learn a little history take this trip thru Hwy 9.
Your first stop is the Merrybrook Lodge that is at best out of the way but close to everything. While there you can traipse over to Felton or Pat Burrell's Boulder Creek where there is a Golf and Country Club. These two towns are still full of charm and tourist attractions including really good BBQ.
Assuming you stay Thursday to Friday in the Merrybrook you will head North on One and land in Saratoga where you can spend a good weekend in La Hacienda Inn but only the bar you will do fine if you hang out at the Toll House in Los Gatos because you will end up at Ruthe's Roberts and then onto the Montalvo Arts Center in Monte Sereno.
No stay at on the Hwy 9 trio of towns would not be complete without breakfast as you walk down main street in Los Gatos which is filled with shops and restaurants enough to feed a small army of dogs and runners.
Head back up Hwy 9 before you leave town to stop in Big Basin Park for a minute and just listen to the world pass you by.