Background Early postpartum discharges increased organically during the COVID-19 pandemic. It is not known if this ‘natural experiment’ of shorter postpartum hospital stays resulted in increased risk for postpartum readmissions and other acute postpartum care utilization such as emergency room encounters. Objective The objectives of this study were to determine which clinical factors were associated with expedited postpartum discharge and whether the expedited postpartum discharge was associated with increased risk for acute postpartum care utilization. Methods This retrospective cohort study evaluated birth hospitalizations at affiliated hospitals during two periods: (i) the apex of the ‘first wave’ of the COVID-19 pandemic in New York City (3/22/20 to 4/30/20) and (ii) a historical control period of one year earlier (3/22/19 to 4/30/19). Routine postpartum discharge was defined as ≥2 d after vaginal birth and ≥3 d after cesarean birth. Expedited discharge was defined as <2 d after vaginal birth and <3 d after cesarean birth. Acute postpartum care utilization was defined as any emergency room visit, obstetric triage visit, or postpartum readmission ≤6 weeks after birth hospitalization discharge. Demographic and clinical variables were compared based on routine versus expedited postpartum discharge. Unadjusted and adjusted logistic regression models were performed to analyze factors associated with (i) expedited discharge and (ii) acute postpartum care utilization. Unadjusted (ORs) and adjusted odds ratios (aORs) with 95% CIs were used as measures of association. Stratified analysis was performed restricted to patients with chronic hypertension, preeclampsia, and gestational hypertension. Results A total of 1,358 birth hospitalizations were included in the analysis, 715 (52.7%) from 2019 and 643 (47.3%) from 2020. Expedited discharge was more common in 2020 than in 2019 (60.3% versus 5.0% of deliveries, p < .01). For 2020, clinical factors significantly associated with a decreased likelihood of expedited discharge included hypertensive disorders of pregnancy (OR 0.40, 95% CI 0.27–0.60), chronic hypertension (OR 0.14, 95% CI 0.06–0.29), and COVID-19 infection (OR 0.51, 95% CI 0.34–0.77). Cesarean (OR 3.00, 95% CI 2.14–4.19) and term birth (OR 3.34, 95% CI 2.03, 5.49) were associated with an increased likelihood of expedited discharge. Most of the associations retained significance in adjusted models. Expedited compared to routine discharge was not associated with significantly different odds of acute postpartum care utilization for 2020 deliveries (5.4% versus 5.9%; OR 0.92, 95% CI 0.47–1.82). Medicaid insurance (OR 2.30, 95% CI 1.06–4.98) and HDP (OR 5.16, 95% CI: 2.60–10.26) were associated with a higher risk of acute postpartum care utilization and retained significance in adjusted analyses. In the stratified analysis restricted to women with hypertensive diagnoses, expedited discharge was associated with significantly increased risk for postpartum readmission (OR 6.09, 95% CI 2.14, 17.33) but not overall acute postpartum care utilization (OR 2.17, 95% CI 1.00, 4.74). Conclusion Expedited postpartum discharge was not associated with increased risk for acute postpartum care utilization. Among women with hypertensive diagnoses, expedited discharge was associated with a higher risk for readmission despite expedited discharge occurring less frequently.