Airbnb Management
Full-service Airbnb management for your short-term rental. Nationwide.
Oshkosh, Wisconsin
In Oshkosh, Wisconsin, guests can find a diverse range of Airbnb accommodations to suit various preferences and budgets. Options include charming historic homes that reflect the city's rich heritage, often located near the scenic shores of Lake Winnebago. For those seeking a more modern stay, there are contemporary apartments and condos in the downtown area, providing easy access to local dining and entertainment. Travelers looking for a cozy, rustic experience can opt for cabins or cottages nestled in the surrounding countryside, offering a peaceful retreat. Additionally, there are budget-friendly private rooms in shared homes, ideal for solo travelers or those looking to meet locals. Whether visitors are in town for the renowned EAA AirVenture event or exploring the local arts scene, Oshkosh's Airbnb offerings provide a comfortable and convenient base.
As of the latest information, Oshkosh, Wisconsin, does not have specific laws governing short-term rentals like Airbnb. However, hosts must comply with general state regulations applicable to short-term rentals. This includes obtaining a seller’s permit from the Wisconsin Department of Revenue and collecting state sales tax, which is 5%, as well as any applicable county taxes. Additionally, hosts may need to collect a local room tax, which in Oshkosh is typically around 10%. It is important for hosts to ensure compliance with any homeowner association rules or lease agreements that may restrict short-term rentals.
Managing an Airbnb in Oshkosh, Wisconsin, involves several key tasks to ensure a successful operation. Hosts need to focus on maintaining the property to provide a clean, comfortable, and welcoming environment for guests, which includes regular cleaning, restocking essentials, and addressing any maintenance issues promptly. Effective communication with guests is crucial, from the initial booking inquiries to providing check-in instructions and addressing any questions or concerns during their stay. Additionally, optimizing the listing with high-quality photos and accurate descriptions can help attract more bookings. Hosts should also stay informed about local regulations and compliance requirements for short-term rentals in Oshkosh to avoid any legal issues. Finally, monitoring guest reviews and feedback is essential for making improvements and maintaining a high rating, which can lead to increased bookings and revenue.
In Oshkosh, Wisconsin, some of the best areas to stay in an Airbnb include the downtown district, which offers a vibrant atmosphere with easy access to local shops, restaurants, and cultural attractions like the Grand Opera House and the Oshkosh Public Museum. The University of Wisconsin-Oshkosh area is another great option, especially for those interested in a lively college-town vibe with plenty of cafes and bars. For a more serene experience, consider staying near Lake Winnebago, where you can enjoy beautiful waterfront views and outdoor activities such as boating and fishing. Each of these areas provides a unique experience, catering to different interests and ensuring a pleasant stay in Oshkosh.
Oshkosh, Wisconsin, presents a promising market for Airbnb investment, primarily due to its vibrant cultural scene and strategic location. The city hosts several annual events, such as the EAA AirVenture Oshkosh, which attracts aviation enthusiasts from around the world, significantly boosting short-term rental demand. Additionally, Oshkosh's proximity to the University of Wisconsin-Oshkosh ensures a steady influx of visitors, including prospective students and their families, as well as academic professionals. The city's picturesque setting along Lake Winnebago and its array of outdoor recreational activities further enhance its appeal to tourists. With relatively affordable property prices compared to larger urban centers, Oshkosh offers a compelling opportunity for investors seeking to capitalize on a growing tourism sector while benefiting from a lower cost of entry.
As of the latest data, the average Airbnb revenue in Oshkosh, Wisconsin, reflects a modest but steady income for hosts, largely influenced by the city's seasonal attractions and events. Oshkosh, known for hosting the annual EAA AirVenture Oshkosh, sees a significant spike in Airbnb bookings and revenue during this period, with many properties experiencing full occupancy and premium pricing. Outside of major events, the revenue tends to stabilize, with hosts earning a consistent income from travelers visiting for the city's natural attractions and university-related activities. Overall, while not as high as in larger metropolitan areas, the average Airbnb revenue in Oshkosh provides a reliable supplementary income for property owners, particularly those who strategically market their listings around key local events.
In Oshkosh, Wisconsin, the occupancy rate for Airbnbs tends to fluctuate with the seasons, reflecting the city's local events and climate. The highest occupancy rates are typically observed during the summer months, particularly in June and July, when the weather is warm and outdoor activities are in full swing. This period coincides with popular events like the EAA AirVenture Oshkosh, which draws aviation enthusiasts from around the world, significantly boosting demand for short-term rentals. Conversely, the winter months see a decline in occupancy rates due to colder weather and fewer events, although the holiday season can bring a temporary uptick. Overall, the Airbnb market in Oshkosh is characterized by a strong seasonal pattern, with peak demand aligning with major events and favorable weather conditions.
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.