A green method for hydroxypropyl-β-cyclodextrin-glycerol-assisted extraction (HCGAE) of bioactive phenolics from S. montana, Lamiaceae was optimized using Box-Behnken design and response surface methodology and compared conventional water/ethanol-based extraction. The procedure was aimed at obtaining extracts with the maximum content of total phenols (TP), flavonoids (TF), dihydroxycinnamic acids (TDCA), rosmarinic acid (RA), and luteolin 7-O-glucoside (LG). The impact of glycerol content (0−70%), 2-hydroxypropyl-β-cyclodextrin content (0−0.4 mmol), temperature (20−70 °C), herbal material weight (0.3−0.8 g), extraction duration (5−25 min), and ultrasound power (144−720 W) on the extraction efficiency was analyzed. Four extracts with maximum amounts of target phenols, OPT-TP (5.93 mg/mL), OPT-TDCA-RA (4.17 mg/mL and 1.16 mg/mL, respectively), OPT-TF (0.99 mg/mL), and OPT-LG (0.28 mg/mL) were prepared. Comparison of the content of TDCA, TF, RA, and LG with those obtained in water/ethanol-based extraction demonstrated the superiority of the HCGAE approach for the extraction of phenols from S. montana. The extracts displayed good anti-elastase and excellent anti-hyaluronidase activity. IC50 values of the anti-hyaluronidase activity (1.67 ± 0.06 μL extract/mL, 1.16 ± 0.08 μL extract/mL, 0.85 ± 0.03 μL extract/mL, and 0.79 ± 0.05 μL extract/mL for OPT-TP, OPT-TDCA-RA, OPT-TF, and OPT-LG, respectively) surpassed that of the applied positive control, tannic acid. The observed bioactivity of the optimized extracts makes them promising active ingredients for natural cosmetics. The results of this research indicate that HCGAE is an excellent alternative to conventional water/ethanol-based extraction of phenolics from Satureja montana L.-yielding extracts with potent anti-elastase and anti-hyaluronidase properties suitable for direct use in cosmetic products.