Hello Bsandberg.
Thank you for using Apple Support Communities. We understand that you're having trouble connecting to hotel Wi-Fi. Allow us to look into this issue with you.
Do you currently have any third-party firewall softwares installed on your Mac? If so, try disabling them to see if that helps. Which macOS version are you currently using with your Mac?
Find out which macOS your Mac is using
If you do have any pending updates available and you're able to connect to a different reliable Wi-Fi network, try updating your Mac to see if that helps address this specific issue while attempting to connect to a Captive Network. Remember to create a backup of your data prior to updating:
Back up your Mac with Time Machine
How to update the software on your Mac
Feel free to keep us updated. Kind regards.