Airbnb Management
Full-service Airbnb management for your short-term rental. Nationwide.
Ashland, Wisconsin
In Ashland, Wisconsin, guests can find a variety of Airbnb accommodations that cater to different preferences and needs. Options range from cozy cabins and rustic cottages nestled in the scenic Northwoods, offering a tranquil retreat for nature lovers, to charming historic homes that reflect the area's rich heritage. For those seeking a more modern stay, there are contemporary apartments and homes equipped with all the necessary amenities. Many of these properties provide easy access to Lake Superior, offering stunning views and opportunities for outdoor activities like fishing, kayaking, and hiking. Whether visitors are looking for a peaceful getaway or a convenient base to explore the local attractions, Ashland's diverse Airbnb offerings provide a welcoming and comfortable experience.
As of the latest information, Ashland, Wisconsin, does not have specific laws governing short-term rentals like Airbnb. However, property owners must comply with general zoning regulations and any applicable state laws regarding short-term rentals. Hosts are typically required to collect and remit state sales tax and local room tax on bookings. Wisconsin imposes a 5% state sales tax, and Ashland may have additional local taxes that apply to short-term rentals. Property owners should ensure they are in compliance with all tax obligations and consider consulting with local authorities or a tax professional for detailed guidance.
Managing an Airbnb in Ashland, Wisconsin, involves several key tasks to ensure a successful and smooth operation. Hosts need to focus on maintaining the property to a high standard, which includes regular cleaning, maintenance, and addressing any repairs promptly to provide a comfortable stay for guests. Effective communication is crucial, requiring timely responses to inquiries and clear instructions for check-in and check-out procedures. Additionally, optimizing the listing with accurate descriptions and appealing photos can attract more guests. Pricing strategies should be adjusted according to seasonal demand and local events to maximize occupancy and revenue. Compliance with local regulations and obtaining necessary permits is essential to avoid legal issues. Lastly, gathering and responding to guest feedback can help improve the service and enhance the overall guest experience.
Ashland, Wisconsin, offers a charming selection of areas for an Airbnb stay, each with its unique appeal. The downtown area is ideal for those who enjoy being close to local shops, restaurants, and the vibrant arts scene, including the historic murals that adorn many buildings. For nature enthusiasts, staying near Chequamegon Bay provides stunning views of Lake Superior and easy access to outdoor activities like hiking and kayaking. The Marengo River area offers a more secluded experience, perfect for those seeking tranquility and a connection with nature. Each of these areas provides a distinct taste of Ashland's welcoming community and natural beauty.
Ashland, Wisconsin, presents a promising opportunity for Airbnb investment due to its picturesque location on the shores of Lake Superior and its proximity to popular attractions like the Apostle Islands National Lakeshore. The city attracts tourists year-round with its outdoor recreational activities, including hiking, fishing, and boating in the summer, and snowmobiling and ice fishing in the winter. Additionally, Ashland's vibrant arts scene, historic architecture, and local events draw visitors seeking a unique cultural experience. The relatively low property prices compared to larger tourist destinations make it an attractive market for investors looking to capitalize on the growing demand for short-term rentals in scenic, less crowded areas.
As of the latest data, the average Airbnb revenue in Ashland, Wisconsin, reflects a modest but steady income for hosts, driven by the city's appeal as a gateway to the natural beauty of the Apostle Islands and Lake Superior. The region's seasonal tourism, particularly during the summer months, boosts occupancy rates and nightly prices, contributing to higher revenues during peak periods. However, the market remains competitive, with hosts needing to offer unique experiences or amenities to stand out. Overall, while not among the highest-earning Airbnb markets, Ashland provides a reliable supplementary income for property owners, especially those who capitalize on the area's outdoor attractions and local events.
Ashland, Wisconsin, experiences a moderate occupancy rate for Airbnbs, with noticeable seasonal fluctuations. The peak season typically occurs during the summer months, from June to August, when tourists flock to the area to enjoy the natural beauty of Lake Superior and the surrounding outdoor activities. During this time, occupancy rates are significantly higher, often reaching near full capacity. In contrast, the winter months see a decline in occupancy as colder weather and snow deter some visitors, although there is still interest from those seeking winter sports and cozy retreats. Spring and fall serve as transitional periods with moderate occupancy, attracting visitors interested in the changing seasons and local events. Overall, Ashland's Airbnb market is characterized by its seasonal appeal, with summer being the most popular time for bookings.
Why Choose Checkmate Rentals?
Other Property Managers | ||
---|---|---|
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 |
What you get with Checkmate Rentals
Attract Guests

Listing on all top booking sites
Targeted digital marketing
High-definition photography
Custom copywriting
Manage Details

Dynamic rate-setting technology
Dedicated reservation agents
24/7 guest service
Consistent, professional cleaning
Stocking guest amenities
Payment processing
Take Care of You

Unlimited owner holds
No fixed contracts
Local staff in every market
Inspections and regular maintenance
Guest screening
Optional short-term rental insurance
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.
Direct Bookings
Earn more year after year as guests book their stay directly on our website.
Housekeeping
Make the perfect first impression with wall-to-wall cleanings before guests arrive.
Inspections
Know your property is guest-ready is top-to-bottom inspections after every booking.
Guest Damage Coverage
Save more when you let us cover accidental guest damage coverage up to $3k.
Smart Home Management
We manage your digital locks & noise monitoring tech in your home.
Fast Listings
Get your home fully listed and ready for guests in as little as 3 days.
Automated Touchpoints
Give guests a seamless experience with automated touchpoints from booking to checkout.
Owner Portal
Stay in the loop on your property with our easy-to-use owner portal that lets you check everything you need.
