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Although many buildings within the Highlands Historic District were not constructed until the 1950s, all adhere to a layout and design concept initiated in 1946. This historic complex represents the last privately owned and operated auto-camp/resort constructed in Grand Teton National Park in the historical period, prior to the initiation of Mission-66 concession-development schemes. It is significant for its association with dude-ranch rustic architecture and with area tourism. Although constructed over the course of three decades, the Highlands buildings are united not only by the carefully planned site layout, but also by the almost exclusive use of log for construction, the frequent inclusion of a front porch in the traditional Rocky Mountain Cabin style, and the simple design and small scale of the cabins. In an example of the overall uniformity of dude-ranch rustic design in Jackson Hole, the cabins bear a striking resemblance to those associated with the neighboring Double Diamond Dude Ranch.

In 1914, Pennsylvania natives Harry and Elizabeth Sensenbach filed a homestead claim to 160 acres along the east bank of Cottonwood Creek. By the late 1920s, in a pattern witnessed throughout Jackson Hole, the Sensenbach's augmented their meager ranching income with tourist dollars, renting a few cabins, and serving ''soft drinks and hard liquor'' to area visitors. Two tourist cabins, a second-generation residence, and the grave site of the Sensenbach's son (on original homestead acreage outside the historic district boundaries), date from this period of the site's history.

Charles Byron and Jeanne Jenkins and Gloria Jenkins Wardell purchased the Highlands site in 1946. From this date until 1956, they methodically added ''one or two cabins a year'' in a U-shaped pattern anchored by a large log/board-and-batten lodge. The lodge, originally envisioned as a ''Tyrollean type'' to conform to the frequent use of Swiss architecture in national parks, was instead constructed in the more typical regional rustic style. The Jenkins sold the Highlands to the National Park Service in 1972. The Park Service converted the buildings to seasonal quarters for temporary employees.