Once you have the homestead site,the cellar hole part is a little easier....alot of the times first a small cabin was built that might have had a cellar beneath it....and then a larger home was built once the homestead got established.....the cellar holes are not huge....small depressions in the ground that more than likely have been filled in with debris and dirt along with the rock walls....and maybe now a tree or two growing out of them. The site would be out of the wind,close to water and probally gave the person a good view...most were built with their door to the East......if you suspect the cellar hole might be in a clearing.....go early in the morning and look at the way the dew lies on the ground reflecting in the sun...it gathers more in a depression and reflects better....It would have had some type of a chimney...which is usually toppled over ...so an abundance of rocks in one area is your first clue .....I have never found a cellar hole with bricks ...only rock. I always look for clues....old pottery or rusting tin that was on the roof ....many of the homesteaders would remove the structure and use the logs for other buildings once their bigger homes were built, then filling in the hole with debris....great places to find bottles.
Pictured below are two cellar holes that are over a hundred years old...you can see how the land has reclaimed them....
I know there are some great hunters here out in New York that seem to have the dibs on the cellar holes finds....read some of those posts and see what they were able to find.