Sea buckthorn (Hippophae rhamnoides L.) is used in beverages, pharmaceuticals, cosmetic products, and animal feeds. Although sea buckthorn has been shown to be easy to propagate vegetatively, currently, there is little information on reliable techniques to vegetatively propagate the plant repetitively within a single year. To address this, three experiments were conducted to study whether season and chilling affected the successful rooting of cuttings. Four cultivars, ‘Chuskaya’, ‘Golden Rain’, ‘Lord’, and ‘Sunny’, were used in the season- and chilling-effect experiments. Hardwood and softwood cuttings from field-grown plants did not root from October to December. The percent of rooted cuttings in January was cultivar-dependent. The number and percent of rooted greenhouse-produced cuttings were significantly affected by length of chilling. Most cuttings were produced and the highest percent rooted when the plants chilled for at least 6 wk. ‘Lord’ had the most and ‘Golden Rain’ the least number of rooted cuttings. This study indicated that greenhouse-grown stock plants were a viable source of sea buckthorn cuttings for vegetative propagation. When combined with field-grown sources, it is possible to produce sea buckthorn planting material year-round.