Not quite what you are looking but if you're interested in Operation Market Garden: for the Dutch maps there is https://www.topotijdreis.nl, which gives you historical maps with a year slider. This can at least help one visualize how cities, villages, and topography at through the years.
There's also tools that wrap a part of toporijdreis and add other georeferenced historical maps! I recently saw one of those at https://geodienst.xyz/pastforward. Wish more people georeferenced historical maps, but it is tough.
