I use Dockertools with OracleVirtualBox on my Window Machine to run OpenStudio-server.

This question might be related.

I havent tryed Vagrant, but I can run the server via docker on windows local virutal machine.

Following is the brief overview what I did, It might depends on the windows version and proxy setting

After installing Dockertools on my windows 8.1 pro machine and run docker deamon, then from the "Docker Quickstart Terminal" in my case,

change directory to the goto pat/OpenStudio-server folder, then type,

docker-compose -f docker-compose.deploy.yml up

If you are lucky the servers are deployed.

You must setup port forwarding in order to access from your local PAT2.0 on windows to the server which is running on the container you just have deployed on the VirtualBox.