Hi @Brian Kinney,
To my knowledge there is no built-in solutions for this.
You may need to use Microsoft Graph scripts to achieve this goal.
Besides, if the main purpose is to enable OOF for these users during holidays, to me another method is to add all users to a csv file, then periodically run a script in Exchange Online Powershell to bulk enable OOF with the Set-MailboxAutoReplyConfiguration cmdlet for these users.
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