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Oakland, MD
Generally Investor Friendly
Local STR Agent
Local STR Agent

YES — Short-term rentals are explicitly allowed in Oakland, Maryland, and throughout Garrett County under the county's Transient Vacation Rental Unit (TVRU) ordinance. The county has maintained a structured regulatory framework since 2006 that permits short-term rentals operating for 14 days or less, subject to specific licensing, safety, and operational requirements.
Garrett County is unique in Maryland as the only county without countywide zoning, but has established comprehensive TVRU regulations that apply throughout the county, including Oakland. Properties must comply with the TVRU licensing requirements to operate legally as short-term rentals.
Oakland hosts earn a median $60,534/year with $524 ADR and 44% occupancy.
Top performers pull in $91,646+ per year.
See the full Oakland market breakdownJohn Groves, Licensing Technician
Lori Paugh (Accommodation Tax Inquiries)
Amanda Klotz (Tax Supervisor)
Maryland Comptroller (State Sales Tax)
Disclaimer: This guide provides general information based on available sources. Regulations may change, and specific circumstances may require additional permits or compliance measures. Always verify current requirements with local authorities and consult legal professionals before making investment decisions.
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Oakland is a small town in western Maryland that serves as the county seat of Garrett County, set amid the forested ridges and hollows of the Appalachian Plateau. The community has a year-round population of roughly 1,900 residents and maintains the quiet, small-town character typical of the Mountain Maryland region, with a walkable historic core and a pace shaped by the surrounding outdoors. It is best known as the gateway to Deep Creek Lake, the largest freshwater lake in the state, and to the network of state parks, ski slopes, and wilderness areas that draw visitors throughout the year. The nearest major city is Pittsburgh, Pennsylvania, located approximately 85 miles to the northwest across the border.
Just a few miles north of town, Deep Creek Lake anchors the area's tourism economy. The roughly 3,900-acre reservoir is a year-round destination, popular for boating, fishing, swimming, and lakeside rentals in the warmer months and transforming into a hub for ice fishing, snowmobiling, and other cold-weather pursuits in winter. Its shoreline communities, public swimming beaches, and a variety of waterfront restaurants make it the single largest draw for visitors to the region, and its proximity to Oakland means guests can enjoy both the convenience of in-town services and the recreational spread of the lake.
A short drive west of Oakland brings visitors to Swallow Falls State Park, one of Maryland's most photographed natural sites. The park is home to Muddy Creek Falls, the tallest free-falling waterfall in the state, along with the Tolling Gate and Swallow Falls themselves, all set within old-growth hemlock and white pine forest along the Youghiogheny River. Roughly a 15-minute drive from town, the park offers hiking trails, picnic areas, and a year-round campground that fills quickly during the summer leaf season.
Just down the road from the lake, Wisp Resort is the area's primary four-season mountain resort. In winter it operates Maryland's only ski mountain, with downhill and cross-country skiing, snow tubing, and ice skating, while the warmer months bring mountain coasters, zip lines, golf, and chairlift rides with views over the lake. Its base area at the foot of Marsh Mountain places it within about a ten-minute drive of Oakland, giving visitors a full slate of resort amenities without having to leave the area.
Oakland's appeal as a short-term rental base comes from this rare combination: a small, authentic mountain town with a walkable historic main street, immediate access to Deep Creek Lake, and a deep bench of outdoor attractions within a short drive in every direction. Guests who stay here can spend the morning on the water, the afternoon chasing waterfalls, and the evening back in town for a local restaurant, all without long transfers between destinations.
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