Do you know if Tolkien ever actually drew maps of certain places in his books? I found a map of Bag End a few minutes ago, but I'm not sure if Tolkien himself did it. I always pictured Bag End as a long tunnel leading straight through the hill with rooms to the left and right, but this looks more like it is built parallel with the path outside his porch; I've also seen a map of Beorn's Halls, but that one has no signature either.
Now I'm not sure if this is good or bad to know - after all the purpose of books is to create images in your own head - but it would still be interesting to become familiar with Tolkien's own imaginations, it doesn't necessarily affect your own personal imaginations in any dramatical way.
I don't know what one can expect to see in the upcoming book The Art of The Hobbit but maybe it will have some maps. The book, edited by Wayne Hammond and Christina Scull, is being published in the United Kingdom later this month and includes about 100 drawings and illustrations Tolkien made for The Hobbit.
The maps he made that I can think of, which have seen publication, including a drawing of the layout of the Teiglin where Turin ambushed Glaurung, Thror's map of Erebor, the map of Wilderland, the maps of Beleriand and Middle-earth (both redrawn by Christopher), the map of the Shire, a map depicting the outline of Bree, the map of Gondor, and the map of Numenor.
-~-~-~-~-~-~-~-~-~-~- Author of Visualizing Middle-earth, Parma Endorion: Essays on Middle-earth, 3rd edition, and Understanding Middle-earth.