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I suppose, but I was thinking something like ssh'ing into Server A, and then locally connecting to Server B.
As long as both are on the same subnet you should have no problem with this. For example, if both machines have 192.168.100.x addresses, then they should be able to communicate directly to one another. Is this not the case?
Another alternative is to set up a port forward over the initial ssh connection, something like:
ssh -L 12345:<lan ip of serverB>:22 serverA
Then from another terminal on your workstation ssh -p 12345 serverA and you should connect to serverB. I use forwarding like this on sites I access remotely for access to any internal computer with sshd, to access a router http configuration screens, etc.