As the center of commerce and legal affairs for Montgomery County, Rockville was a fine locale for hotels. Beginning in the 1750s, travelers, courthouse clientele, salesmen, and visitors to the Court House town stayed at Lawrence Owen's ordinary, Charles Hungerford's tavern, Francis Kidwell's Farmers Hotel, the Washington Hotel, the Union Hotel (rebuilt as the Corcoran), the Montgomery House, and others.

The arrival of the B&O railroad in 1873 changed the town. Rockville became a destination for city-dwellers wanting to spend a weekend, holiday, or summer in the country. In addition to the hotels around Court House Square, summer visitors took rooms in local boarding houses or made arrangements to stay in private homes.

In 1886, Charles G. Willson purchased five acres west of the town of Rockville, hired an architect, and began to build a large, four-story brick "summer boarding house." Before the building was completed, Willson filed for bankruptcy. Among those looking at the building were the Trustees of the Rockville Academy. The unfinished hotel and adjoining three acres were bought for $6,000 by Mary J. Colley, proprietress of the Clarendon Hotel in Washington, D.C., and her partner Charles W. Bell.

When the Woodlawn Hotel opened for business in the spring of 1889, it was an immediate success. Summer guests, many of whom were prominent D.C. residents, enjoyed social gatherings, musical soirees, card games, dances, walks among the trees and cool country breezes. Ads for the Woodlawn boasted electric bells, gas lighting, artesian water, fresh country vegetables, breezy porches, and 40 guest rooms. Visitors usually came by train, traveling the mile from the railroad station to the hotel by carriage.

Rockville's "boom" continued into the Gay Nineties, until a series of depressions deflated the economy. Many summer boarders, such as Edwin and Lucy Smith, decided to build year-round residences on lots in new subdivisions opening around Rockville. They liked living in a small town convenient to federal government jobs in Washington. However, by 1906, the Woodlawn's owners, heavily in debt, had to sell. The hotel, stable, windmill, ice house, carriage house, laundry and servants quarters, and eight acres went to public auction.

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