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Generally Investor friendly
STRs are explicitly permitted citywide/countywide with no caps, but require an annual zoning certificate, initial inspection, hotel tax registration, on-site parking, and a manager within 25 miles. The process uses a streamlined online portal but includes mandatory steps and annual renewals, making compliance moderately complex yet predictable.
Local STR Agent
STR specialist · Centreville, MD
Centreville, Maryland, is a small historic town that serves as the county seat of Queen Anne's County, located on the Eastern Shore of the Chesapeake Bay. With a population of approximately 4,500 residents, it has the quiet, traditional character of a mid-Atlantic county seat, with a compact historic downtown, tree-shaded streets, and well-preserved 18th- and 19th-century architecture. Positioned about 70 to 80 miles east of Baltimore and Washington, D.C., across the Chesapeake Bay Bridge, Centreville functions as a low-key gateway to the Eastern Shore's farmlands, waterways, and historic villages.
Just outside town in Wye Mills, Wye Oak State Park preserves the site where one of the largest white oak trees in the United States stood for more than four centuries before toppling in 2002. A descendant of the original tree has been planted nearby, and the site remains a small but meaningful stop for visitors interested in natural history. The park is roughly a ten-minute drive from the Centreville town center, along with the surrounding Wye Plantation lands that trace their roots to colonial-era estates.
South of Centreville along the Eastern Shore's scenic byways lies the historic waterfront town of St. Michaels, about a 30-minute drive. Known for its harbor, boutique inns, and the Chesapeake Bay Maritime Museum, St. Michaels draws visitors year-round and serves as a hub for boat tours, oyster industry exhibits, and seasonal events on the Miles River. The town has a reputation as one of the most photographed destinations on the Eastern Shore, with a working boatyard, a historic lighthouse, and a small downtown clustered around a central marina.
A short drive further south brings travelers to Easton, a larger town that functions as the cultural center of the mid-Shore. Its historic district features art galleries, the restored Avalon Theatre, and a stretch of restaurants and shops. Closer to Centreville, Tuckahoe State Park offers a wooded retreat for hiking, fishing, and paddling along the Choptank River watershed, with the park's main entrance a roughly 20-minute drive south of the town center.
Centreville's appeal as a short-term rental market rests on its combination of small-town tranquility and proximity to a wide variety of Eastern Shore experiences. Guests can spend a morning in Centreville's quiet historic core, an afternoon exploring St. Michaels' maritime heritage or Easton's arts scene, and evenings sampling regional cuisine without retracing their steps. With the Chesapeake Bay Bridge connecting the region to the Washington-Baltimore urban corridor in roughly 90 minutes to two hours, the town offers an easy escape into a slower, water-oriented way of life.