(1) Background: Cold-hardy interspecific hybrid grapes (CIHG) are well adapted to the Annapolis Valley edaphoclimatic conditions. The main characteristics of CIHG are the high bud hardiness tolerance to winter frost, the short growing cycle, and the good tolerance to cryptogamic diseases. Based on local experience, the Vitis vinifera varieties should be grown in the warmest areas of the Annapolis Valley (Nova Scotia, Canada). Despite this, there is little scientific evidence that shows the viticultural behavior of these varieties under the edaphoclimatic conditions of this valley. (2) Methods: Thus, the aim of this research was to evaluate the viticultural behavior of two CIHG (L’Acadie and New York Muscat) and three V. vinifera varieties (Chardonnay, Riesling, and Pinot Noir) growing in the Annapolis Valley over three consecutive seasons. (3) Results: The coldest season (2019) produced a delay in grapevine phenology of at least 18 days for budburst compared to the warm seasons (2017 and 2018). In addition, in the coldest season from budburst to bloom the duration decreased compared to the rest of the seasons. The main phenological stages started earlier in L’Acadie than in the V. vinifera varieties. L’Acadie presented lower N petiole content than the V. vinifera varieties, which conditioned shoot growth in the studied seasons. CIHG presented low B petiole levels and produced musts with low malic acid content, while V. vinifera varieties produced musts with high N content. L’Acadie was the only variety that could bud out, and differentially produced fruit after the spring frost of −2 to −3 °C for 2 h in 2018 in this trial. (4) Conclusions: L’Acadie, and to a lesser extent, Riesling, hold an interesting adaptation to the edaphoclimatic conditions of the Annapolis Valley.