If the two Windows machines are on the same L2 (VLAN and subnet), it should be a fairly simple flow.
What you've described is very typical of Windows firewall (especially Windows server) - blocking all inbound ping requests. For testing, I would disable the firewall completely.
Other than that, I would start by:
- Check ARP on both machines to verify whether they have address resolution for eachother. In cmd, type "arp -a"
and check for the other machine's IP.
- Run up wireshark on both machines and run a ping from one to the other to determine which direction the ping is failing.
From the above tests, you should be able to verify whether the issue is a machine not replying or the switch blocking a ping request/reply. That way you can focus your troubleshooting to the appropriate device.