I don't agree with Ian (or what you say he said that $\mathbb{P}(B_t\in A|B_0 = B_a)$ is not a random variable). Indeed, we have:
$$\begin{align}
\mathbb{P}(B_t\in A|B_0 = B_a) &= \mathbb{P}(\{(B_t-B_0)+B_a\in A\}|B_0 = B_a)\\
&= \mathbb{P}(\{X+B_a\in A\}|B_0 = B_a)\\
&=\mathbb{E}(\mathbb{I}_{\{X+B_a\in A\}}|B_0 = B_a)
\end{align}
$$
with $X$ is a random varible independent to $B_a$ (which is also a random variable).
Then, $\mathbb{I}_{\{X+B_a\in A\}}$ is a random variable.
According to the definition of conditionnal expectation, $\mathbb{E}(\mathbb{I}_{\{X+B_a\in A\}}|B_0 = B_a)$ is a random variable because there exists a function $f$ such that
$$\mathbb{E}(\mathbb{I}_{\{X+B_a\in A\}}|B_0 = B_a) = f(B_a)$$
and $f(B_a)$ is a random variable.
$$$$
Return back to your initial question in this post, the answer should be
$$
\begin{align}
\mathbb P\left(\sup_{t\in [a,b]}B_t>x \right) &=\mathbb P\left(\sup_{t\in [a,b]}(B_t-B_a) + B_a>x\right) \\
&=\mathbb P\left(\sup_{t\in [0,b-a]}(W_t) + B_a>x\right) \\
&=\mathbb E\left( \mathbb{I}_{\left \{\sup_{t\in [0,b-a]}(W_t) + B_a>x\right\}} \right) \\
&=\mathbb E\left(\mathbb{E}\left( \mathbb{I}_{\left \{\sup_{t\in [0,b-a]}(W_t) + B_a>x\right\}}|B_a \right)\right) \\
&=\mathbb E\left(\mathbb{P}\left( \sup_{t\in [0,b-a]}(W_t) + B_a>x|B_a \right)\right) \\
\end{align}
$$
Here, $W_t$ is second Brownian motion which is independent to the Brownian motion $B_t$ (I think this notation $W_t$ is necessary to remove all ambiguity)
And you will find that the conditional probability $\mathbb{P}\left( \sup_{t\in [0,b-a]}(W_t) + B_a>x|B_a \right)$ is a random variable (this probability is equivalent to the one in your question $\mathbb{P}(B_t\in A|B_0 = B_a)$).
Of course, $\mathbb E\left(\mathbb{P}\left( \sup_{t\in [0,b-a]}(W_t) + B_a>x|B_a \right)\right)$ (the expectation of a random variable) is a number, which is consistent with the fact that $\mathbb P\left(\sup_{t\in [a,b]}B_t>x \right) $ is a number.