AMS–dated sediment cores combined with ground–penetrating radar profiles from two lakes in southeastern Massachusetts demonstrate that regional water levels rose and fell multiple times during the Holocene when the known climatic controls (i.e., ice extent and insolation) underwent unidirectional changes. The lakes were lowest between 10,000 and 9000 and between 5500 and 3000 cal yr B.P. Using a heuristic moisture-budget model, we explore the hypothesis that changes in seasonal precipitation regimes, driven by monotonic trends in ice extent and insolation, plausibly explain the multiple lake-level changes. Simulated lake levels resulting from low summer precipitation rates match observed low lake levels of 10,000–9000 cal yr B.P., whereas a model experiment that simply shifts the seasonality of the modern Massachusetts precipitation regime (i.e., moving the peak monthly precipitation from winter to summer) produces levels that are ∼2 m lower than today as observed for 5500–3000 cal yr B.P. The influence of the Laurentide ice sheet could explain dry summers before ca. 8000 cal yr B.P. A later shift from a summer-wet to a winter-wet moisture-balance regime could have resulted from insolation-driven changes in the influence of the Bermuda subtropical high. Temperature changes probably further modified lake levels by affecting snowmelt and transpiration.