I've stayed at a different hotel each year for the last 4 years, in order:
Fairfield Inn & Suites (Airport): Just the girlfriend and myself. Not a bad place; had decent breakfast (and a Waffle House across the street if we felt our arteries were being too healthy). About a 10 minute drive. Our first GenCon (well, I went once in '95 when it was in WI.)
Crowne Plaza: Our first taste of downtown, so we can understand why the demand is so crazy. Nice, short, skywalk to the ICC and to the vendor hall. The biggest downside was the floors were hard for those who ended up there; bring a good sleeping bag or air mattress. Otherwise, really nice location. We had no issue with noise.
The Alexander: Really nice hotel. Nice, large rooms, comfy beds, and lots to look at if you get bored and want to look at walls. It was a bit of a walk to the ICC, especially in the August weather. We took the South Street path, so there was an Arby's and White Castle within easy walking distance. This was my first year running game events, so hauling my map case, etc, was a bit of a pain in the neck, but wasn't too bad. Worse was hauling stuff back after a trip to the vendor hall. That said, I'd totally stay there again. They often had fruit-infused water in the lobby area -- it's a small thing, but it was quite nice after that walk. The cost was a bit more than I had wanted, but it was gotten outside the housing block, so can't really complain. Parking wasn't cheap either, but not the highest in Indy by a bit.
Holiday Inn Express & Suites: Another really nice hotel, suprisingly. This is the first year we had more than 2-3 of us, as I brought my sister and her boyfriend as well, so we ended up in a suite with a total of 5 guests. Super comfy, plenty of room, wasn't too costly (considering I got it outside the housing lottery) and the breakfast was rather nice, if a bit crowded. Since it's right next to the Lucas stadium, it was a very short walk. Since True Dungeon is now at the stadium, it'll be really nice for those staying there. Parking was the cheapest, easily at $14 per night, if I remember correctly.
This is the first year that I've actually gotten a room from the housing lottery and we'll be staying at the JW. Since my games are almost always end up there, it'll be really nice to not have to haul my map/bags all over the ICC and can easily get to my room. Will be eager to see how the rest of it pans out; a bit meh about the lack of free Wi-fi, but to be honest, we rarely used it at the other places anyways. There were games to play, afterall...