Airbnb Management
Full-service Airbnb management for your short-term rental. Nationwide.
Baileys Harbor, Wisconsin
In Baileys Harbor, Wisconsin, guests can find a variety of Airbnb accommodations that cater to different preferences and group sizes. Options range from cozy cabins and rustic cottages nestled in the woods, perfect for those seeking a tranquil retreat, to charming lakefront homes offering stunning views of Lake Michigan. Visitors can also choose from modern condos and spacious family homes, ideal for larger groups or families looking for a comfortable stay with all the amenities. Many of these properties highlight the natural beauty of Door County, with easy access to outdoor activities such as hiking, fishing, and kayaking, making them an excellent choice for nature enthusiasts. Whether seeking a romantic getaway or a family vacation, Baileys Harbor offers diverse Airbnb options to suit various tastes and budgets.
As of the latest information, Baileys Harbor, Wisconsin, does not have specific local laws governing Airbnb or short-term rentals. However, property owners must comply with Door County regulations and Wisconsin state laws. In Wisconsin, short-term rental operators are required to obtain a seller’s permit and collect state sales tax, which is 5%, as well as any applicable county and local room taxes. Door County imposes an additional room tax, which is currently set at 5.5%. Property owners should also ensure compliance with zoning regulations and any homeowner association rules that may apply. It is advisable for hosts to stay informed about any changes in local ordinances or state laws that could affect short-term rental operations.
Managing an Airbnb in Baileys Harbor, Wisconsin, involves several key tasks to ensure a smooth operation and positive guest experience. Hosts need to focus on maintaining the property, which includes regular cleaning, landscaping, and addressing any maintenance issues promptly. Effective communication with guests is crucial, from providing clear check-in instructions to being responsive to inquiries and concerns. Marketing the property through appealing listings and high-quality photos can help attract more guests, especially during peak tourist seasons. Additionally, staying informed about local regulations and ensuring compliance with any short-term rental laws is essential. Finally, managing bookings, setting competitive pricing, and gathering guest feedback for continuous improvement are vital components of successful Airbnb management in this scenic location.
Baileys Harbor, Wisconsin, offers a charming and serene getaway with several ideal areas for an Airbnb stay. The downtown area is perfect for those who want to be close to local shops, restaurants, and the picturesque marina, providing a quaint small-town feel with easy access to amenities. For nature enthusiasts, staying near the Ridges Sanctuary or Toft Point State Natural Area offers a peaceful retreat with opportunities for hiking and birdwatching. Additionally, the shoreline along Kangaroo Lake provides stunning waterfront views and a tranquil setting, ideal for those looking to relax by the water. Each of these areas offers a unique experience, making Baileys Harbor a versatile destination for various preferences.
Baileys Harbor, Wisconsin, is an attractive market for Airbnb investment due to its picturesque location on the Door County peninsula, known for its natural beauty and outdoor recreational activities. The area draws tourists year-round with its charming small-town atmosphere, access to Lake Michigan, and proximity to popular attractions like the Ridges Sanctuary and Cana Island Lighthouse. The demand for short-term rentals is bolstered by seasonal events, such as festivals and art fairs, which attract visitors looking for unique and cozy accommodations. Investors can benefit from the relatively lower property prices compared to more urban areas, while still capitalizing on the steady influx of tourists seeking a peaceful retreat in a scenic environment.
Baileys Harbor, Wisconsin, a charming destination in Door County, offers a variety of Airbnb accommodations that cater to tourists seeking a peaceful retreat. The average Airbnb revenue in Baileys Harbor can vary significantly depending on factors such as the season, property type, and location. During peak tourist seasons, such as summer and fall, when visitors flock to enjoy the natural beauty and local attractions, hosts often experience higher occupancy rates and increased nightly rates, boosting their revenue. Conversely, the off-season may see a dip in bookings and revenue. On average, hosts in Baileys Harbor can expect moderate earnings, with those offering unique or premium accommodations potentially earning above the local average. However, specific revenue figures can fluctuate based on market trends and individual property performance.
Baileys Harbor, Wisconsin, experiences a notable fluctuation in Airbnb occupancy rates due to its seasonal appeal, primarily driven by its location in Door County, a popular tourist destination. The occupancy rates tend to peak during the summer months, from June to August, when visitors flock to the area for its scenic beauty, outdoor activities, and festivals. This period often sees occupancy rates reaching their highest levels as tourists seek accommodations near the picturesque Lake Michigan shoreline and the surrounding natural attractions. Conversely, the winter months, particularly from December to February, typically see a decline in occupancy rates as the colder weather and reduced tourist activities lead to fewer visitors. However, the fall season, especially during the leaf-peeping period in October, can also see a temporary spike in occupancy as travelers visit to enjoy the vibrant autumn foliage. Overall, Baileys Harbor's Airbnb market is characterized by its strong summer demand and moderate off-season activity.
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.