Duration of the drought period is important for plant response during drought and after rewatering. We hypothesized that, if drought duration is extended, (1) high seedling vigor and rapid development of a deep root system will not be advantageous, and (2) osmotic adjustment will be more important. Six diverse rice (Oryza sativa L.) genotypes were selected from rainfed lowland germplasms to examine the development of a deep root system and osmotic adjustment, and their relationship with biomass production during drought and after rewatering, under two different drought durations (shorter and prolonged) in the greenhouse. NSG19 and KDML105 had greater seedling vigor (larger seedling biomass), developed a deep root system earlier in response to drought, extracted soil water more quickly, and their pre-dawn leaf water potential declined more rapidly during the prolonged drought period. These two genotypes showed superior drought recovery even after a prolonged drought period in which they suffered a greater reduction in transpiration, water use efficiency, and biomass production. The superior recovery ability was associated with larger plant size by the end of the drought period rather than with plant water status during drought, such as osmotic adjustment or leaf water potential. Osmotic adjustment was greater during prolonged drought periods (ca. 0.7 MPa) than during shorter drought periods (ca. 0.5 MPa), and lower osmotic adjustment was mostly associated with a higher leaf water potential. Genotypic variation in osmotic adjustment was observed, but there was no clear relationship between osmotic adjustment and biomass production during drought periods. These patterns of response of rice seedlings to drought and rewatering in the greenhouse should help to explain the patterns of adaptation of rainfed lowland rice in the field. Selection for drought recovery ability should be an advantageous strategy for early season drought.