If you decide to travel around on a regular basis, become loyal to one brand and join their rewards program. We frequent the Hilton brand of hotels, but regardless of whether you choose Hilton, Marriott, Sheraton etc, once you start racking up points, they can be converted into free stays.
Before we head somewhere for a race, even if it's in our own backyard, we always Google a 'Top Ten Things to Do in..." list. Spending a little time up front means you can find the things that interest you, plan efficiently and make sure you hit the highlights. You don't have to spend a lot of money - we usually look for farmer's markets, parks, hikes etc.