I drive my '65 Dodge fairly often, and have left it outside at hotels around Maryland, PA, and Delaware in the past without issue. I usually try to choose rooms where I can walk right to my car from the room. I always back into the parking spot, and have numerous anti theft "plans" in place to disable the vehicle.

In all honesty, I know you want the experience of driving your vehicle there, but if you're going to have a chase truck, take the fuel money you'd spend on the car, and buy an open car trailer. When you get back home, you can sell it and recoup most, if not all of your investment in the trailer.