Statistics for occurrence #1 of “Winter Hill” in chapter 14 of Historic leaves, volume 5, April, 1906 - January, 1907:

...
By Frank M. Hawes The teachers of the summer schools outside the Neck were: Miss Mary E. Brown, of the Winter Hill ; Elizabeth P. Whittredge, of Prospect Hill; Miss Mary Dodge, of Milk Row; Miss Clara D. Whittemore, of the Russell; and Miss Hannah S. Austin, of the Gardner. These schools were assigned to the car...
Max. Freq. Min. Freq.
Entity Corpus Doc Corpus Doc  
Winter Hill (Wyoming, United States) 80 46 0 0 0 user votes
Winter Hill (Massachusetts, United States) 372 42 0 0 0 user votes
Winter Hill (United Kingdom) 6 0 0 0 0 user votes
Winter Hill (Maine, United States) 4 0 0 0 0 user votes
Winter Hill (Massachusetts, United States) 0 0 0 0 0 user votes

† This entity has been selected by the automated classifier as the most likely match in this context. It may or may not be the correct match.