(1) Background: Nursing Home (NH) residents are a population with health and social vulnerabilities, for whom emergency department visits or hospitalization near the end of life can be considered a marker of healthcare aggressiveness. With the present study, we intend to identify and characterize acute care transitions in the last year of life in Portuguese NH residents, to characterize care integration between the different care levels, and identify predictors of death at hospital and potentially burdensome transitions; (2) Methods: a retrospective after-death study was performed, covering 18 months prior to the emergence of the COVID-19 pandemic, in a nationwide sample of Portuguese NH with 614 residents; (3) Results: 176 deceased patients were included. More than half of NH residents died at hospital. One-third experienced a potentially burdensome care transition in the last 3 days of life, and 48.3% in the last 90 days. Younger age and higher technical staff support were associated with death at hospital and a higher likelihood of burdensome transitions in the last year of life, and Palliative Care team support with less. Advanced Care planning was almost absent; (4) Conclusions: The studied population was frail and old without advance directives in place, and subject to frequent hospitalization and potentially burdensome transitions near the end of life. Unlike other studies, staff provisioning did not improve the outcomes. The results may be related to a low social and professional awareness of Palliative Care and warrant further study.