When I was in college, I purchased the Red Shift program, which featured a nifty model of the sky with information about many of the shiny dots in space. I even utilized the model to determine the make-up of the night sky for a location I was using in a book I was writing (I finished writing the book (working title: Sparkwood and 21) about eight years ago. I now plan to publish it unedited on the Web. There is a lot of fun stuff in it, but a lot of unfortunate stuff too. I am working on something much more intense and focused now. I hope to finish it this year with a first draft, but I don't have much time to work on it, so its slow-going but fun).
Technology has changed significantly since Red Shift, but I don't think the improvements of these sky models are quite there yet. Google Sky, Stellarium, and the Sloan Digital Sky Survey on NASA World Wind are fun, but incomplete. They are not as intuitive and transformative as their Earth-bound counterparts.
However, we may on the cusp of a breakthrough. At TED, Microsoft previewed the Worldwide Telescope. The presentation did not floor me, but I read here that it will utilize the Photosynth technology (related links here and here). This adds the promise of 3D views of some of these space objects, which could revolutionize desktop astronomy viewing. I'll be looking forward to its release.