Yes, Hilton offers free room upgrades as a key benefit for its Gold and Diamond members, though they are always subject to "space availability" at the time of check-in. In 2026, Hilton's updated policy introduces a new tier called Diamond Reserve, which grants even higher priority for these upgrades and a "Confirmable Upgrade Reward" that can be used at the time of booking for a stay of up to 7 nights. For standard Gold and Diamond members, upgrades typically include moves to "preferred" rooms, such as those on higher floors, rooms with better views, or even Executive Floor rooms with lounge access. While Diamond members are technically eligible for upgrades up to a one-bedroom suite, it is important to note that these are never guaranteed and depend entirely on the hotel's occupancy levels. At high-end brands like Waldorf Astoria or Conrad, upgrades are often more conservative due to limited suite inventory. To maximize your chances, it is recommended to check in via the Hilton Honors app as soon as the window opens, as many hotels now process digital "automatic upgrades" up to 72 hours before arrival.