Despite extensive documentation of the reentry challenges facing female prisoners, few such studies have focused on women exiting jails. The Window Study investigated factors associated with the perceived availability of stable housing upon release from detention. Anonymous surveys were conducted with a random sample (n = 148) of female detainees at the Baltimore City Detention Center from January 21 to March 17, 2005. Interviews focused on socio-demographic background, health status, recent drug use and sexual behavior history, and material and social resource availability upon release. The median age of female detainees was 37 (interquartile range [IQR]: 29, 41), 69% were African-American, and 33% identified as lesbian or bisexual. The median income in the 30 days prior to arrest was $145 (IQR: 0, 559), and the median number of prior arrests was 5 (IQR: 3, 11). In the presence of other variables familial support (Adjusted Odds Ratio [AOR] 2.57; 95% Confidence Interval [CI] 1.21, 5.47) and a monthly income of $400-799 (AOR 3.18; 95% CI 1.00, 10.07) were positively associated with perceived housing stability upon release; wanting a support group for having traded sex for money, drugs or a place to stay (AOR 0.25; 95% CI 0.10, 0.63) was significantly negatively associated with perceived housing stability upon release. This study suggests the importance of pre-release planning and continuity of care for female detainees. Interventions should emphasize access to housing, economic opportunity and family reunification. Special attention is warranted to those who have engaged in sex work, who may be marginalized from family and service-based support networks.