I have seen part of it done once for booking slots for a Christmas Grotto. But that was quite a specific requirement, without the need for the same item (in that case a time slot) to be recycled.
We looked at doing something similar for a client as while back (a Bed & Breakfast) but didn't as the client was only looking for the booking piece and not online payments. We came to the conclusion that since all the new work would be in the booking module and he wouldn't be using the existing functionality in Zen Cart, it just wasn't the right solution in that case.
Basically the booking and processing that goes around that doesn't fit comfortably with Zen Cart's product structure. It's on our (Kuroi Web Design's) "one day" list, as we see requests for this regularly and feel that it would be a useful addition that could then feed naturally into Zen Cart's product and payment processing functionality.
That said, there are a number of stand-alone booking modules out there, but typcially they address a specific industry segment, so producing one generic approach that isn't impossibly complex to configure may prove challenging and that's why I doubt that you will find something fitting your specific requirement for Zen Cart already available "off-the-shelf".
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