The Observer Hotel demonstrates the rebuilding of the Rocks in the post-plague era. It is a reasonably well-preserved example of a small, formerly on bar, hotel. It demonstrates changing drinking habits by the gradual expansion of the drinking facilities and loss of Women's and Guest's Parlours. It embodies a fragment of The Rocks social history by virtue of the need to protect patrons by incorporating internally supervised lavatories.
It embodies changes to The Rocks in the loss of its residential component. It represents changes in laws governing accommodation on licensed premises by virtue of the new (1950s) second floor bathroom and WC. It is an important functioning remnant of the many hotels which once dotted The Rocks.