This study examined the relation between method of weight loss and long‐term maintenance among successful weight losers enrolled in a weight‐loss maintenance trial. Participants were 186 adults (mean age = 51.6 ± 10.7 years, mean BMI = 28.6 ± 4.7 kg/m2) enrolled in the STOP Regain trial who had lost at least 10% of their body weight in the past 2 years using a very low‐calorie diet (VLCD; n = 24), commercial program (n = 95), or self‐guided approach (n = 67). Participants were randomized to a weight‐maintenance intervention delivered face to face or over the internet or to a newsletter control condition, and followed for 18 months. At study entry, individuals who had used a VLCD had achieved a weight loss of 24% of their maximum weight within the past 2 years compared to 17% achieved by those who had used a commercial program or self‐guided approach (P < 0.001). However, individuals who had used a VLCD regained significantly more weight than the other two groups and by 6 months, there were no significant differences in overall percent weight loss (i.e., initial weight loss and maintenance) between VLCD, commercial, and self‐guided methods. In contrast, individuals who had used a self‐guided approach maintained their weight losses from baseline through 18 months. The large initial weight losses achieved by individuals who had used a VLCD were not maintained over time, whereas individuals who had used a self‐guided approach maintained their initial weight losses with the greatest success. The generalizability of these findings is limited by the sizeable weight losses achieved by study participants.