Of course you can. The basic steps are as follows:
Download The Installer
Just go to Setup > Desktop Integration > Salesforce for Outlook, and download the latest installer.
Create Shared Folder
Create a new folder on the server, share it with users in the domain, and put the installer there. Note: You need to get the "msi" file, not the exe. To get this file, use
SalesforceForOutlook /extract on the command-line, as outlined in Salesforce for Outlook Silent Installation
Create Group Policy Object
Go to Start > Administrative Tools > Active Directory Users and Computers.
Right-click on your domain, and choose Properties.
On the Group Policy tab, click New. Give it a name, like Salesforce for Outlook.
Now, click on Properties, and choose the Security tab. Select the groups you want to apply this GPO to.
Next, you need to edit the GPO, choose Computer Configuration > Software Settings.
In the Open dialog, select the full network name and file of the share you created with the installer file. This must the be the full share name (e.g.
\\adserver\installers\salesforceoutlook.msi), which you can't get to by simply using the Browse button; you need to type in the full name of the file.
Click Assigned to assign the installer to the selected groups.
If you get stuck (this is the condensed version), try reading How to use Group Policy to remotely install software in Windows Server 2008 and in Windows Server 2003. While I haven't tried this extensively, it should work as advertised.