Hoping to spur tourism and promote business development, Starkville's Chamber of Commerce led an effort to organize the Starkville Hotel Corporation and raise funds through stock subscriptions. The building was constructed at a cost of $80,000 between 1924 and 1925, and the hotel was furnished at an additional cost of $15,000. The hotel was named in honor of Chamber of Commerce President Chester Jarnigan.
In 1940, the hotel changed its name in honor of John Stark, the Revolutionary War hero for whom the city is also named. The Stark Hotel was operated by the Starkville Hotel Corporation until 1965, when it sold the property to John Curtis Page. The hotel changed hands multiple times in the subsequent three decades, serving as business offices, retail space, and student apartments before being renovated by its new owners in the early 2000s. The building then was then returned to its original purpose as a hotel, continuing to serve guests today.
In recent years, Hotel Chester has been expanded to include a popular restaurant. The Beer Garden was designed and created by Gordon Ramsay and features his famous Gordon Burger. The restaurant is located off of North Lafayette Street, in a public parking lot. It features both indoor and outdoor seating, locally brewed craft beers, and a relaxed atmosphere that draws in both new and returning patrons.