Here's a very fast way:

result = ((((12 * n + 45) * n + 50) * n + 15) * n - 2) * n // 120

How I got there:

1. Rewrite the inner sum as the well-known x*(x+1)//2. So the whole thing becomes sum(x**2 * x*(x+1)//2 for x in range(n+1)).
2. Rewrite to sum(x**4 + x**3 for x in range(n+1)) // 2.
3. Look up formulas for sum(x**4) and sum(x**3).
4. Simplify the resulting mess to (12*n**5 + 45*n**4 + 50*n**3 + 15*n**2 - 2*n) // 120.
5. Horner it.

Another way to derive it if after steps 1. and 2. you know it's a polynomial of degree 5:

3. Compute six values with a naive implementation.
4. Compute the polynomial from the six equations with six unknowns (the polynomial coefficients). I did it similarly to this, but my matrix A is left-right mirrored compared to that, and I called my y-vector b.

Code:

from fractions import Fraction
import math
from functools import reduce

def naive(n):
    return sum(x**2 * sum(range(x+1)) for x in range(n+1))

def lcm(ints):
    return reduce(lambda r, i: r * i // math.gcd(r, i), ints)

def polynomial(xys):
    xs, ys = zip(*xys)
    n = len(xs)
    A = [[Fraction(x**i) for i in range(n)] for x in xs]
    b = list(ys)
    for _ in range(2):
        for i0 in range(n):
            for i in range(i0 + 1, n):
                f = A[i][i0] / A[i0][i0]
                for j in range(i0, n):
                    A[i][j] -= f * A[i0][j]
                b[i] -= f * b[i0]
        A = [row[::-1] for row in A[::-1]]
        b.reverse()
    coeffs = [b[i] / A[i][i] for i in range(n)]
    denominator = lcm(c.denominator for c in coeffs)
    coeffs = [int(c * denominator) for c in coeffs]
    horner = str(coeffs[-1])
    for c in coeffs[-2::-1]:
        horner += ' * n'
        if c:
            horner = f"({horner} {'+' if c > 0 else '-'} {abs(c)})"
    return f'{horner} // {denominator}'

print(polynomial((x, naive(x)) for x in range(6)))

Output (Try it online!):

((((12 * n + 45) * n + 50) * n + 15) * n - 2) * n // 120

(fastest methods, 3 and 4, are at the end)

In a fast NumPy method you need to specify dtype=np.object so that NumPy does not convert Python int to its own dtypes (np.int64 or others). It will now give you correct results (checked it up to N=100000).

# method #2
start=time.time()
w=np.arange(0, n+1, dtype=np.object)
result2 = (w**2*np.cumsum(w)).sum()
print('Fast method:', time.time()-start)

Your fast solution is significantly faster than the slow one. Yes, for large N's, but already at N=100 it is like 8 times faster:

start=time.time()
for i in range(100):
    result1 = summation(0, n, mysum)
print('Slow method:', time.time()-start)

# method #2
start=time.time()
for i in range(100):
    w=np.arange(0, n+1, dtype=np.object)
    result2 = (w**2*np.cumsum(w)).sum()
print('Fast method:', time.time()-start)

Slow method: 0.06906533241271973
Fast method: 0.008007287979125977

EDIT: Even faster method (by KellyBundy, the Pumpkin) is by using pure python. Turns out NumPy has no advantage here, because it has no vectorized code for np.objects.

# method #3
import itertools
start=time.time()
for i in range(100):
    result3 = sum(x*x * ysum for x, ysum in enumerate(itertools.accumulate(range(n+1))))
print('Faster, pure python:', (time.time()-start))

Faster, pure python: 0.0009944438934326172

EDIT2: Forss noticed that numpy fast method can be optimized by using x*x instead of x**2. For N > 200 it is faster than pure Python method. For N < 200 it is slower than pure Python method (the exact value of boundary may depend on machine, on mine it was 200, its best to check it yourself):

# method #4
start=time.time()
for i in range(100):
    w = np.arange(0, n+1, dtype=np.object)
    result2 = (w*w*np.cumsum(w)).sum()
print('Fast method x*x:', time.time()-start)

Comparing Python with WolframAlpha like that is unfair, since Wolfram will simplify the equation before computing.

Fortunately, the Python ecosystem knows no limits, so you can use SymPy:

from sympy import summation
from sympy import symbols

n, x, y = symbols("n,x,y")
eq = summation(x ** 2 * summation(y, (y, 0, x)), (x, 0, n))
eq.evalf(subs={"n": 1000})

It will compute the expected result almost instantly: 100375416791650. This is because SymPy simplifies the equation for you, just like Wolfram does. See the value of eq:

@Kelly Bundy's answer is awesome, but if you are like me and use a calculator to compute 2 + 2, then you will love SymPy ❤. As you can see, it gets you to the same results with just 3 lines of code and is a solution that would also work for other more complex cases.