I live in the county and usually go to the show on Wed. so don't have any experience with the weekend crowds. There are, of course, hotels and B and B's in Shipshewana, but you will find several motels at the intersection of the Toll Road and highway 9-north of Howe.
Just a note. Near Shipshewana is the little town of Emma. Go south of Shipshewana on highway 5, several miles south of highway 20, and turn left/east at the sign for Emma. It is about a mile.You will find an old time café on the southeast corner of the main intersection. It will not be crowded like the restaurants in Shipshe. Two doors south of the café you will find an Amish fabric store.
On the county road going into Emma is Yoder Popcorn's outlet store.