A caboose is nice, but how about a converted locomotive overlooking the railroad? This amazing converted locomotive is one of the lodging options at the Izaak Walton Inn in Essex, Montana, which is easily reached on what they say is the last remaining flag stop on the Amtrak system. As they say, "About a quarter of guests at the Izaak Walton Inn arrive via... the Empire Builder." We could stop over on our way back from Chicon 8, for example, stay a few days, then continue on to the Pacific Northwest (offhand, probably Portland) as part of a circular trip like the one we're doing this year.
Regrettably, there appear to be no stores in Essex, so one would need a car to go buy supplies to take advantage of the fully-equipped kitchen. Also, it would be the most expensive hotel room we've ever rented (>$300/night), even assuming we could get a reservation — it being singular means that getting a booking would be challenging. But it still looks like a lot of fun and a beautiful place to visit.
And no, we're not bidding the Inn as a site for a Westercon, or even a SMOFCon, even though it probably has better rail and air (nearest airport is Kalispell MT) access than Tonopah.