Hi Amanda,
I'd invite you to check out BookThatApp. This is a booking engine we built specifically to work with Shopify. I believe we'd be able to meet your requirements with the App, with some additional customization to suit your specific needs.
We have a site that does a similar upcoming event listing: http://www.theschool.com.au/apps/bookthatapp/calendar
We welcome you to try it out on your store on our free trial plan, or if you'd like to discuss further please contact us via info @ shopifyconcierge.com.
Thanks, Gavin.
