No, you can't tell you're accelerating. But you can tell when things are accelerating relative to one another.
Imagine you're falling towards the planet, but you set it up to begin with so you're surrounded by a sphere of stones, which are also falling freely. From your point of view, what happens?
The stones at the top are slightly further from the planet, so they're in less gravity. You accelerate more rapidly than the stones, so from your point of view, they accelerate upwards away from you. Similarly, the stones below you accelerate down away from you. The stones to the side are getting a slightly different direction of gravitational field, at a small inward angle, so they appear to get accelerated towards you as everything is pulled to the centre of the planet.
So the sphere appears to deform into an ellipsiodal sort of shape. But you are not measuring the acceleration here, but the relative acceleration. The larger the sphere, the more obvious the effect will become. In the limit of a very small sphere, you see no measurable effect and you can't see anything that tells you you aren't in deep space. This is the equivalence principle. What destroys the 'inertialness' is the effect of tidal forces, which are anisotropies in the gravitational field.
Your suspicion over the equivalence principle is well founded. While it has a decent mathematical formulation (spacetime is a Lorentzian manifold) it's physical basis is perhaps a little bit woolly. As I alluded to in my previous post it's the same as the statement that a small enough patch of a sphere is flat, which is a statement of approximation rather than absolute fact.