Your requirement of allocating 2 resources at the same time for one booking is currently not possible using the WooCommerce Bookings plugin.
However, WooCommerce bookings by PluginHive provides a lot of customisation packages using which you might be able to achieve your business requirement.
You can check out their customisation packages from here: https://www.pluginhive.com/product/customization-for-pluginhive-woocommerce-plugins/
Alternatively, you can also reach out to PluginHive booking experts team from here: https://www.pluginhive.com/support/ and they will definitely help you out in how to achieve your business requirement.