If you book thru MS, yes, only if you have your two ressies linked together so you dont have to move out of your room(if you book the same type room).
No, if you dont link the two ressies together and you move into a new room.
If you book cash thru wdw you would not be guarantee to stay in the same room, you may have to move. If you book thru wdw and want the dining plan you would have to purchase a one day basic ticket for 71.95.
booking dining thru ms no ticket is required to be purchase.