Digging a bit deeper in problem, I tried printing the Eigenvalues of the Cov matrix.
print np.linalg.eigvalsh(Cov)
And the answer turns out to be this
[-0.0801339 -0.0801339 0.12653595 0.12653595 0.12653595 0.12653595 0.14847999 0.36269785 0.36269785 0.36269785 0.36269785 1.09439988 1.09439988 1.09439988 1.09439988 9.6772531 ]
Aha! Notice the first two negative eigenvalues? Now, a matrix is positive definite if and only if all its eigenvalues are positive. So, the problem with the matrix is not that it's close to 'zero', but that it's 'negative'. To extend @duffymo analogy, this is linear algebra equivalent of trying to take square root of negative number.
Now, let's try to perform same operation, but this time with scipy.
scipy.linalg.cholesky(Cov, lower=True)
And that fails saying something more
numpy.linalg.linalg.LinAlgError: 12-th leading minor not positive definite
That's telling something more, (though I couldn't really understand why it's complaining about 12-th minor).
Bottom line, the matrix is not quite close to 'zero' but is more like 'negative'