A few thoughts... Santa Clara zone has two 4* hotels---the Hyatt and Hilton---and both are active on Priceline. Those are business oriented hotels, so often cheaper on Friday/Saturday/Sunday nights (as low as $45) than weekdays, but sometimes good weekday deals on Priceline too. As a general approach you might decide which nights you want to go to Great America and Raging Waters and bid for those nights in Santa Clara zone first. Then deal with the other nights. As for the other nights... It sounds like you want a "Downtown" type of experience...walking distance to stores and restaurants. Unfortunately Priceline's San Jose zone doesn't just include Downtown San Jose but also the airport area. Bidding 4* in the San Jose zone you're likely to get the Doubletree, which is a nice place but it's an "airport hotel", kind of a sterile area with not much to see or do for visitors. Not a walking area. The 4* Montgomery sounds more like what you're looking for---a restored classic hotel Downtown and walking distance from museums, restaurants, etc. But no guarantee you'd win the Montgomery on Priceline. I think the Doubletree comes up more often. If you want to stay Downtown let us know the dates are and maybe we can identify a Downtown hotel for you on Hotwire. Also if you don't mind the drive I think either the Cypress or Moorpark Hotels in the Cupertino/Campbell zone would work. Or try for a 4* in Los Gatos. Hardly anyone bids there but the Priceline 4* hotel must be Hotel Los Gatos. It's a very upscale area, but still casual feeling with sidewalk cafes, galleries, boutiques all within strolling distance of the hotel. (Los Gatos doesn't appear as a zone on Priceline's San Jose page. You have to enter Los Gatos as your destination.)