Never stayed at the Herald Square so no opinions. My family of 5 with 3 kids (ages 15, 12 and 9) stayed at the HH Chelsea last year and it was a great base to explore Manhattan. We stayed in two rooms. Although the property does not have connecting rooms, they were able to assign us rooms connected by a shared hallway with a door. Both room keys can access the hallway door. We preferred the shared hallway vs connecting rooms. Happy to answer any questions you may have about the HH Chelsea.