Winter survival of temperate-zone woody perennials requires them to resist loss of frost hardiness (deacclimation) during winter and early spring thaws. However, little is known about deacclimation response in woody landscape plants. Moreover, what impact, if any, the degree of deacclimation has on reacclimation capacity has not been systematically studied. We used nine genotypes of deciduous azaleas (Rhododendron subgenus Pentanthera) to investigate effects of deacclimating conditions on bud cold hardiness and reacclimation ability. Dormant floral buds, with 3–5 cm stem attached, were collected in late December from field-grown plants, and placed in constant warm [22 °C 15 °C (D/N)] and humid conditions for increasing durations (0-day to 14-day) to stimulate deacclimation. Bud cold hardiness (lt50) was determined (using logistic regressions) by evaluating immature flower survival at subfreezing treatment temperatures. Results indicated that azalea genotypes from colder provenances showed greater initial frost hardiness. Typically northern genotypes had slow to intermediate deacclimation rates, while rates of southern genotypes were intermediate to rapid. High initial frost hardiness was frequently associated with slow deacclimation. Buds retained the capacity to reacclimate upon cold exposure [2 °C/–2 °C; (12 h/12 h)] even after 8 days of deacclimation. Distinct differences were observed between the two latitudinal ecotypes of R. viscosum with respect to their initial bud hardiness, deacclimation rates, and reacclimation capacities. We suggest that the three attributes, i.e., high initial hardiness, slow deacclimation, and high reacclimation capacity, together may be important for winter-survival of azalea buds.