Gluten-free breads are characterized by a rapid staling and short shelf-life, therefore increasing bread waste. To reduce staling, physically and/or chemically modified starches were incorporated at 10 and 20% levels in gluten-free breads. Di-starch phosphate (DP), acetylated di-starch adipate (ADA), and pregelatinized acetylated di-starch phosphate (PADP) were used. All modified starches at 10% of replacement and 20% ADA starch decreased crumb hardness and increased cohesiveness not only on the same day of baking but also after 7-days of storage. Conversely, breads with 20% PADP starch, with a lower specific volume, due to greater dough viscoelastic behavior, showed harder and less cohesive crumbs. Moisture loss ranged from day 0–7 from 6.4 to 11.0%, being especially significant in low-volume breads. Calorimetry results denoted a lower propensity of ADA and PADP starches to retrograde (amylopectin retrogradation) compared to DP, due to the dual cross-linking/acetylation modification. Among all starches, ADA was the most promising starch for reducing and delaying hardness and loss of cohesiveness in breads, with hardness (20% ADA) at day 7 similar to control at day 1.