I dunno if your IC status or points help here http://www.harborcourt.com/ I'm not up on that program at all. Barring actual free nights, though, this room's gonna be out of your price range, I suspect, especially on race weekend.

I usually Priceline a hotel in the Inner Harbor, and after getting a crappy room at the Wyndham as a 3* bid a few years ago I only bid 4* down there. I've had good stays at the Hyatt (under $60 in Feb) and the Marriott Waterfront (something like $70-75 in summer, but in both cases these rates were last minute, bid the day of my stay). The latter is slightly less convenient if you're trying to walk from public transit. Other possibilities are the Sheraton and I think one other.

The Holiday Inn BWI is fine, too. I've gotten that one on dirt cheap bids, like 40 bucks, but many times when I'm there (as long as nothing's going on) BWI is actually harder to get a reasonably priced room. For Preakness weekend, though, rates are probably all jacked up accordingly. Floating bids probably won't even work this far out, but maybe. I've never bid anything anywhere close to this far out, so I just don't know. A few months was really my longest ever lead time for bidding. There are some even lower end properties at BWI like Microtel, Fairfield, Homestead (shudder, I've stayed at that one, don't recomend). I don't think there's a place around BWI that won't shuttle you back to the airport/light rail. There's really a ton of rooms in the BWI area, so worth checking for rates. Inner Harbor's going to be way better for the sightseeing and bar hopping day, though, I would think, unless you do go down to DC (in which case BWI is better). You'll just have to decide if the price is worth the tradeoff. If you can take the risk of Priceline (and pay this far in advance, which may be the bigger risk unless you're 100% sure of the trip), you might want to try it for the Inner Harbor 4*. Bidding is not necessarily a good option if you need a room with two beds, though. You have less of a chance that you'll get your choice with this vs with a regular reservation. I'm usually alone or with GF so it doesn't matter what bed type I get.