Does OpenStudio support multiple standalone buildings?

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EnergyPlus and OpenStudio do not require all the zones to be adjacent to each other, so yes, you can model multiple buildings like an elemetry/secondary school campus in a single model. If you want to see consumption by building you would have to add in meters associated with the zones that makeup a particular building.

Having said that you can do this, I wouldn't advise for example modeling a large collage campus as a single OpenStudio or EnergyPlus model. For this use case there are number of urban design tools for performing energy analysis on neighborhoods or districts such as URBANopt which uses OpenStudio as one of its engines.