Looks like your problem is either network-related (firweall or some device is killing this connection between you and the server), but more likely the problem is on the server end.
Operation timed out usually means it tried to make a connection (and the connection wasn't refused) but waited so long to "hear back" from the server that it just had to stop waiting and abort.
Don't use a password. Generate a passphrase-less SSH key and push it to your VM.
If you already have an SSH key, you can skip this step…
Just hit Enter for the key and both passphrases:
$ ssh-keygen -t rsa -b 2048
Generating public/private rsa key pair.
Enter file in which to save the key (/home/username/.ssh/id_rsa):
Enter passphrase (empty for no passphrase):
Enter same passphrase again:
Your identification has been saved in /home/username/.ssh/id_rsa.
Your public key has been saved in /home/username/.ssh/id_rsa.pub.
Copy your keys to the target server:
$ ssh-copy-id id@server
id@server's password:
Now try logging into the machine, with ssh 'id@server', and check-in:
.ssh/authorized_keys
Note: If you don't have .ssh dir and authorized_keys file, you need to create it first
to make sure we haven’t added extra keys that you weren’t expecting.
Finally, check to log in…
$ ssh id@server
id@server:~$
You may also want to look into using ssh-agent if you want to try keeping your keys protected with a passphrase.
Best Answer
Yes, just go into 'System Preferences', select 'Sharing' and enable 'Remote Login'.