Strange though it may seem, remote.it connections to Samba services, whether running on a Windows machine or a Linux machine with Samba installed, will not work when the client is a Windows machine.
remote.it connections generate a hostname and port pair. The Windows OS will not accept the use of an explicit port when attempting to connect to a networked file system.
As a workaround, you can set up a VPN using remote.it. When you set up a VPN, your client joins the target network, and access to Windows shares should work as though they were on your local LAN.