Airbnb Management
Full-service Airbnb management for your short-term rental. Nationwide.
Oxford, Maryland
In Oxford, Maryland, guests can find a variety of Airbnb accommodations that cater to different preferences and group sizes. The town offers charming historic homes and cottages, often featuring classic Eastern Shore architecture, which provide a cozy and authentic local experience. Many of these properties are waterfront or have easy access to the Tred Avon River, offering stunning views and opportunities for boating or kayaking. Additionally, there are modern homes and renovated barns that blend contemporary amenities with rustic charm, ideal for families or larger groups. Some Airbnbs also offer unique features such as private docks, swimming pools, or expansive gardens, enhancing the tranquil and picturesque setting of this quaint town. Whether seeking a romantic getaway or a family retreat, visitors can find accommodations that reflect the serene and historic character of Oxford.
In Oxford, 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 Oxford does not have its own distinct short-term rental tax, hosts are required to collect and remit Maryland's state sales tax, which is 6%, and any applicable county taxes. It's important for hosts to ensure they are in compliance with all relevant tax obligations and to stay informed about any potential changes in local regulations that could affect short-term rental operations.
Managing an Airbnb in Oxford, Maryland, involves several key tasks to ensure a smooth operation and a positive guest experience. Hosts need to focus on maintaining the property by ensuring it is clean, well-stocked, and in good repair, which may involve hiring 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 seasonal demand and local events to remain competitive. Additionally, compliance with local regulations and tax requirements is essential, as is managing reviews and feedback to maintain a high rating and attract future guests. Engaging with the local community and staying informed about tourism trends in Oxford can also enhance the overall guest experience and business success.
Oxford, Maryland, is a charming and historic town on the Eastern Shore, offering a serene getaway with picturesque waterfront views. The best areas to stay in an Airbnb include the heart of Oxford, where you can enjoy easy access to the town's quaint shops, local eateries, and the scenic Oxford-Bellevue Ferry. Staying near the Strand waterfront area provides beautiful views of the Tred Avon River and opportunities for leisurely walks along the shoreline. For those seeking a more secluded experience, consider accommodations near the outskirts of town, where you can enjoy the tranquility of the surrounding countryside while still being a short drive from Oxford's main attractions.
Oxford, Maryland, is a charming and historic town located on the Eastern Shore, making it an attractive market for Airbnb investment. Known for its picturesque waterfront views, quaint streets, and rich maritime history, Oxford draws visitors seeking a peaceful retreat. The town's proximity to the Chesapeake Bay and its reputation for sailing and boating activities enhance its appeal. Additionally, Oxford's small-town charm, with its boutique shops, local eateries, and historic sites, provides a unique experience for guests. Investors can capitalize on the demand for short-term rentals, particularly during peak tourist seasons, by offering accommodations that highlight the town's serene and scenic environment.
As of the latest data, Oxford, Maryland, a quaint and picturesque town known for its maritime heritage and serene landscapes, has seen a moderate performance in its Airbnb market. The average revenue for Airbnb hosts in Oxford tends to reflect the town's seasonal tourism patterns, with higher earnings typically observed during the warmer months when visitors flock to enjoy the Chesapeake Bay and local attractions. Hosts in Oxford often capitalize on the town's charm and proximity to water activities, which can lead to increased bookings and revenue during peak tourist seasons. However, given the town's small size and niche appeal, the overall average revenue remains modest compared to larger, more urbanized areas.
Oxford, Maryland, a small and picturesque town on the Eastern Shore, experiences a relatively stable but modest Airbnb occupancy rate, with notable fluctuations due to its seasonal appeal. The town's peak season typically aligns with the warmer months, from late spring through early fall, when visitors are drawn to its charming waterfront, historic sites, and outdoor activities. During this period, occupancy rates tend to rise as tourists seek short-term rentals for weekend getaways and vacations. Conversely, the colder months see a decline in occupancy, as the town's attractions are less frequented, leading to lower demand for Airbnb accommodations. Overall, Oxford's Airbnb market reflects the town's seasonal tourism patterns, with higher occupancy in the warmer months and a quieter rental scene in the off-season.
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.