With Outlook, if you are connecting to an Exchange server (eg at your office) there might be another problem - hotels sometimes block the port Outlook uses for this. You can overcome this by selecting an option "Connect to my Exchange mailbox using HTTP". It's deep inside some options in the mail setup, hidden very well.
The fact that my company is using an MS Exchange server means I cannot just decide to switch to Thunderbird, etc. I was led to believe that it's Outlook only.
I always use a VPN to connect to my company, as I work from home when not on the road. We used to use the Checkpoint VPN. Always worked from home - I mean 100% of the time. Also worked from most hotels. Every once in a while, there would be a hotel where Outlook would not connect. The VPN seemed to connect fine, but Outlook would never connect and sync. This is with a VPN. Exact same connection method used at home. For example, I stayed at the Marriott Courtyard in Edmonton probably a dozen times - never got an Outlook connection while staying there. Always had to use Web-based mail.
Any ideas as to what the hotel ISP could be doing that could block connectivity through a VPN?
We no longer use a VPN, and have now switched to PPTP connections. Have not had any problems at hotels, yet.