To have multiple maps, you must create a collection. A workshop collection is essentially a set of workshop items. Additionally, you will have to modify the startup command for your server.
These are the requirements:
A Workshop Collection containing the desired maps.
A Steam API Key, which can be obtained from this link.
Let's first create the collection.
- Go to the CS2 Collections page here.
 - Click "Create Collection" and add the maps you want to that collection.
 - Get the Collection ID from the URL (using the same method as getting the map ID)
 
Now that you have your Collection ID, it's time to make alterations to your startup command. Additionally, you will need to obtain your Steam API key from this source. Your modified startup command should resemble something like this.
Here is the link on how to create a custom commandline: https://billing.streamline-servers.com/knowledgebase/4169/Creating-Custom-Commandlines.html

Save the custom commandline and select it on the next page. The commandline font will become bold once it has been selected.