Airbnb Management
Full-service Airbnb management for your short-term rental. Nationwide.
Oakland, Maryland
In Oakland, Maryland, guests can find a variety of Airbnb accommodations that cater to different preferences and needs. The area offers charming cabins and cottages, often nestled in the scenic landscapes of the Appalachian Mountains, providing a cozy and rustic retreat for nature lovers. Many of these properties are located near Deep Creek Lake, offering easy access to outdoor activities such as hiking, fishing, and skiing. Additionally, visitors can choose from modern homes and apartments in the town center, which provide convenient access to local shops, restaurants, and cultural attractions. For those seeking a unique experience, there are also farm stays and historic homes available, allowing guests to immerse themselves in the local heritage and rural charm of the region.
In Oakland, Maryland, there are no specific local laws governing the operation of Airbnbs or short-term rentals. However, property owners must comply with general state and county regulations that may apply to rental properties, such as safety and health standards. While there are no distinct local taxes for short-term rentals in Oakland, hosts are required to collect and remit the state’s 6% sales tax and the 5% Garrett County accommodation tax on the rental income. It is advisable for hosts to stay informed about any changes in local regulations or tax requirements that may affect their operations.
Managing an Airbnb in Oakland, Maryland, involves several key tasks to ensure a smooth operation and positive guest experiences. Hosts need to maintain the property by ensuring it is clean, well-stocked, and in good repair, which may involve coordinating with local cleaning and maintenance services. Effective communication with guests is crucial, from promptly responding to inquiries and booking requests to providing detailed check-in instructions and local recommendations. Pricing strategies should be regularly reviewed and adjusted based on local events, seasonality, and market trends to maximize occupancy and revenue. Additionally, compliance with local regulations and tax requirements is essential to avoid legal issues. Implementing a reliable system for guest reviews and feedback can help improve the property’s reputation and attract more bookings.
Oakland, Maryland, offers a charming and serene getaway, with several ideal areas for an Airbnb stay. Deep Creek Lake is a top choice, known for its stunning natural beauty and outdoor activities like boating, fishing, and hiking. Staying near the lake provides easy access to the state park and a variety of water sports. The downtown Oakland area is another excellent option, offering a quaint, small-town atmosphere with historic architecture, local shops, and cozy cafes. This area is perfect for those who enjoy exploring local culture and history. Additionally, the nearby Wisp Resort area is ideal for visitors interested in skiing and winter sports, providing a convenient location for accessing the slopes and enjoying the resort's amenities. Each of these areas offers a unique experience, catering to different interests and ensuring a memorable stay in Oakland.
Oakland, Maryland, presents a promising opportunity for Airbnb investment, particularly due to its proximity to Deep Creek Lake, a popular year-round destination for outdoor enthusiasts. The area's appeal is bolstered by its scenic landscapes, offering activities such as boating, fishing, skiing, and hiking, which attract a steady stream of visitors. Additionally, Oakland's charming small-town atmosphere, with its historic sites and local festivals, enhances its attractiveness to tourists seeking a quaint getaway. Investors can capitalize on the demand for short-term rentals by targeting properties near the lake or within the town's historic district, ensuring a blend of natural beauty and cultural experiences for guests. The relatively lower property prices compared to larger urban markets also make Oakland an appealing choice for those looking to enter the vacation rental market with a potentially high return on investment.
As of the latest data, the average Airbnb revenue for properties in Oakland, Maryland, reflects a modest yet steady income stream for hosts. This picturesque town, known for its proximity to Deep Creek Lake and various outdoor activities, attracts a consistent flow of visitors, particularly during peak seasons such as summer and winter. Hosts in Oakland typically see higher revenues during these times due to increased demand for vacation rentals. The average monthly revenue can vary significantly based on factors such as property size, location, amenities offered, and the level of competition in the area. Overall, while not as high as in major urban centers, the Airbnb market in Oakland provides a reliable supplementary income for property owners, especially those who capitalize on the area's natural attractions and seasonal tourism.
Oakland, Maryland, experiences a notable fluctuation in Airbnb occupancy rates due to its seasonal appeal, particularly influenced by its proximity to Deep Creek Lake and the surrounding natural attractions. During the peak summer months and the fall foliage season, occupancy rates tend to be high as tourists flock to the area for outdoor activities such as boating, hiking, and enjoying the scenic beauty. Winter also sees a surge in bookings, driven by visitors interested in skiing and other winter sports at nearby resorts. Conversely, the shoulder seasons of late fall and early spring typically witness a dip in occupancy, as the weather becomes less predictable and outdoor activities are less appealing. Overall, the Airbnb market in Oakland is characterized by its strong seasonal demand, with occupancy rates peaking during the summer and winter months.
Why Choose Checkmate Rentals?
![]() | Other Property Managers | |
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Cost | Starting at 15% fee | 25-40% fee |
Guest Communications | Guest response within 10 minutes, 24 hours a day | Sporadic guest communications |
Host Communications | Designated host call in phone line | Bot response assistants |
Insurance | Full damage protection for every reservation | Unreliable insurance coverage |
Contract | No annual agreements | Contract lock-ins |
Checkmate Rentals

Attract Guests
List on top booking sites
Optimize listings for SEO
Feature show-stopping photos
Competitive, dynamic pricing
Mangage Operations
Tailored pricing algorithms
24/7 guest service
Reliable, professional cleaning
Restocking & inventory management
Maintenance coordination


Host Care
Unlimited owner stays
Flexible contract options
East to use host portal
Set it and forget it billing
Exclusive insurance discounts via our partner network
Get in touch with us.

Checkmate Rentals is a full-service property manager. That means the Airbnb listing, the home, the guest and the work is our responsibility.
Local Team Support
Know that you have a friendly, accessible team right up the road to handle any property needs.
Guest Screenings
Book only the most qualified guests 25 and over who’ll enjoy your home the right way.
Unlimited Owner Use
Block off your vacation days with ease, and enjoy your home as often as you want.
Reliable Property Maintenance
Keep your home running smoothly around the clock with a fast, reliable maintenance team.
Transparent Finances
Transparent Finances Booking payouts get paid directly to you for full financial transparency. We never handle your money.
Fast 24/7 Guest Communication
Make every guest feel cared for with industry best response times of 1-15 minutes day and night.
Marketing
Target, attract & book qualified guests with photography, email marketing, and optimized listings.
Revenue Management
Get the competitive edge with dynamic pricing and rates optimized daily by your pricing manager.

Ready to make the jump?
Let's get started! Schedule a call today to learn more about Checkmate Rentals.