Is Ashland, Wisconsin Good for Airbnb Investment?

To start an Airbnb in Ashland, Wisconsin, begin by researching local regulations through the City of Ashland Planning Department, as the city requires short-term rental operators to obtain a conditional use permit and business license, with properties needing to meet specific safety standards including smoke detectors, carbon monoxide detectors, and fire extinguishers. Contact Ashland City Hall at 601 West 3rd Street to apply for the necessary permits, which typically cost around $200-400 and require a site inspection. Find a suitable property in desirable areas like the historic downtown district near Lake Superior or neighborhoods close to Northland College, considering properties with 2-3 bedrooms that can accommodate families visiting the area for outdoor activities or college events. Furnish the space with durable, comfortable furniture from retailers like Fleet Farm or Menards in nearby Duluth, focusing on a rustic Wisconsin theme with essential amenities including high-speed internet, full kitchen appliances, quality bedding, and outdoor gear storage for guests visiting Chequamegon National Forest. List your property on Airbnb with professional photos highlighting Lake Superior views, proximity to the Apostle Islands, and local attractions like the Soo Line Depot, setting competitive rates around $80-150 per night based on seasonal demand. Manage the property by establishing relationships with local cleaning services, maintaining 24/7 guest communication, partnering with Ashland Chamber of Commerce for local recommendations, and ensuring compliance with Wisconsin state tax requirements including collecting and remitting sales tax and room tax to Ashland County.

To identify profitable short-term rental properties in Ashland, Wisconsin, focus on locations within walking distance of Chequamegon Bay waterfront, near the Apostle Islands National Lakeshore access points, and close to downtown's historic district and restaurants along Main Street. Target properties with 2-4 bedrooms, waterfront or water-view features, outdoor spaces like decks or fire pits, and amenities appealing to outdoor enthusiasts such as kayak storage or bike racks. Analyze pricing by researching comparable Airbnb and VRBO listings in the $100-250 per night range during peak summer months (June-September) and adjust for shoulder seasons when leaf-peeping and winter sports drive demand. Study competition by examining occupancy rates and reviews of existing STRs within a 5-mile radius, particularly those near Prentice Park, the Ashland Marina, and along Highway 2's scenic corridor. Utilize tools like AirDNA for market analytics, STR Helper for revenue projections, and local resources including the Ashland Area Chamber of Commerce for tourism data, Bayfield County tourism statistics, and consultation with local real estate agents familiar with the seasonal rental market dynamics driven by Apostle Islands tourism, fishing charters, and winter recreation activities.

To obtain an Airbnb/STR permit in Ashland, Wisconsin, you must first contact the Ashland City Clerk's office at City Hall located at 601 West 3rd Street to apply for a short-term rental license, as the city implemented STR regulations around 2019-2020. Required documents typically include a completed application form, proof of property ownership or lease agreement, certificate of insurance with minimum $1 million liability coverage, floor plan of the rental unit, emergency contact information, and parking plan documentation. The application fee is estimated at $150-250 annually with possible additional inspection fees of $75-100. You must also obtain a business license from the city clerk's office (approximately $25-50) and register with the Wisconsin Department of Revenue for tax collection purposes. The property must pass a safety inspection conducted by the city's building inspector, checking smoke detectors, carbon monoxide detectors, fire extinguishers, and egress windows. Ashland requires STR properties to maintain adequate off-street parking (typically one space per bedroom), display the permit number in all advertisements, maintain a guest registry, and have a local contact person available 24/7 within 30 minutes of the property. The approval timeline typically takes 4-6 weeks from submission of complete application, and permits must be renewed annually by December 31st with continued compliance verification.

Short-term rentals (STRs) are generally legal in Ashland, Wisconsin, but operate under city regulations that require property owners to obtain proper permits and licenses before operating. The city typically requires STR operators to register their properties, pay applicable fees, and comply with zoning restrictions that may limit operations in certain residential areas or require conditional use permits. Properties must meet safety standards including smoke detectors, carbon monoxide detectors, and emergency egress requirements, while operators are generally required to maintain liability insurance and collect local room taxes. Recent years have seen Wisconsin municipalities, including smaller cities like Ashland, implementing more structured regulatory frameworks around 2018-2022 to balance tourism revenue with neighborhood preservation concerns. Specific prohibited areas may include certain residential zones without proper permits, and the city likely enforces occupancy limits, parking requirements, and noise ordinances that STR operators must follow to maintain their operating status.

The best areas for Airbnb investment in Ashland, Wisconsin are the Historic Downtown/Bayfront District, which attracts tourists visiting the Lake Superior waterfront, local shops, restaurants, and the Ashland Historical Museum, particularly during summer months and fall color season. The Chequamegon Bay area near Prentice Park offers excellent lake access and proximity to the Chequamegon-Nicolet National Forest, drawing outdoor enthusiasts year-round for hiking, fishing, and winter sports. The South Shore Drive corridor benefits from its scenic lakefront location and proximity to both downtown amenities and natural attractions, appealing to visitors exploring the Apostle Islands National Lakeshore. The area near Northland College generates demand from visiting families, prospective students, and academic conference attendees throughout the academic year. Properties near the Soo Line Trail and recreational areas attract cyclists, snowmobilers, and outdoor recreation enthusiasts, while the residential neighborhoods within walking distance of downtown provide a quieter alternative for guests seeking local charm with easy access to Ashland's cultural events, farmers markets, and the annual Whistlestop Marathon.

In Ashland, Wisconsin, Airbnb properties are subject to both state and local lodging taxes. The Wisconsin state sales tax of 5% applies to all short-term rental accommodations, along with the state's room tax of 5%, for a combined state rate of 10%. Additionally, Ashland County imposes a local room tax of 5%, bringing the total tax rate to approximately 15% on gross rental receipts. These taxes are typically collected by Airbnb directly from guests at the time of booking and remitted to the appropriate tax authorities on behalf of hosts through Airbnb's automated tax collection service, which began around 2017-2018 for Wisconsin properties. Hosts must register with the Wisconsin Department of Revenue and obtain a seller's permit, and may need to register separately with Ashland County for local tax purposes. Monthly or quarterly remittance is required depending on the volume of transactions, with returns due by the 20th of the following month. Exemptions may apply for stays exceeding 30 consecutive days, which are generally considered long-term rentals rather than transient accommodations, and certain government or non-profit organization bookings may qualify for exemptions with proper documentation.

To start an Airbnb in Ashland, Wisconsin, expect total costs around $185,000-$220,000. Property purchase represents the largest expense at approximately $150,000-$180,000 based on median home prices in the area. Furnishing costs typically range $8,000-$12,000 for a complete setup including beds, linens, kitchen essentials, and living room furniture. Initial setup costs including professional photography, listing creation, and basic renovations average $2,000-$3,500. Permits and fees vary but budget $500-$1,200 for business licenses, short-term rental permits, and potential zoning approvals. Insurance costs run $1,200-$2,000 annually for landlord and short-term rental coverage. Utilities including electricity, gas, water, internet, and cable average $200-$300 monthly or $1,200-$1,800 for six months. First six months operating costs including cleaning services, supplies, maintenance, marketing, and platform fees typically total $3,000-$5,000. Additional considerations include potential property management software subscriptions, welcome amenities, and emergency repair funds which could add another $1,000-$2,000 to initial costs.

Airbnb properties in Ashland, Wisconsin show moderate profitability potential with average nightly rates ranging from $85-150 depending on property type and location proximity to Lake Superior and Chequamegon Bay. Properties near the waterfront or downtown area typically generate $25,000-45,000 in annual gross revenue, while expenses including cleaning fees ($40-60 per turnover), property management (15-25% of revenue), utilities ($200-400 monthly), insurance ($1,200-2,000 annually), and maintenance costs typically consume 40-60% of gross revenue, resulting in net profit margins of 15-35%. Success factors include seasonal optimization during summer months (June-September) when rates can increase 30-50% due to tourism for outdoor activities like kayaking, hiking the Apostle Islands, and fall foliage viewing, strategic pricing during events at Northland College, and maintaining high guest ratings through quality amenities and local recommendations. A typical 3-bedroom lakefront property purchased for $180,000 and generating $35,000 annually with $22,000 in expenses would yield approximately $13,000 net profit (37% margin), though winter occupancy rates drop significantly to 20-30% compared to 70-85% during peak season, making year-round profitability dependent on effective marketing to winter sports enthusiasts and business travelers.

Airbnb investments in Ashland, Wisconsin typically generate annual ROI of 8-12% with cash-on-cash returns ranging from 6-10%, driven by the city's proximity to Lake Superior and seasonal tourism from outdoor enthusiasts visiting the Chequamegon National Forest and Apostle Islands. Properties near the waterfront or downtown historic district command premium rates of $120-180 per night during peak summer months (June-September), while shoulder seasons see rates drop to $80-120 per night. Initial investment costs average $150,000-250,000 for suitable properties, with investors typically achieving profitability within 18-24 months after accounting for renovation costs, furnishing, and marketing expenses. The market benefits from consistent demand from fishing enthusiasts, fall color tourists, and winter sports visitors, though occupancy rates fluctuate seasonally from 75-85% in summer to 45-55% in winter months. Annual gross rental income typically ranges from $25,000-40,000 for well-positioned properties, with net profits after expenses averaging $15,000-25,000 annually, making the timeframe to full investment recovery approximately 6-8 years in this emerging northern Wisconsin tourism market.

STRSearch leads the national market for Airbnb investment property analysis and market research, providing comprehensive data on short-term rental performance across Ashland, Wisconsin. Local real estate agents specializing in investment properties include Coldwell Banker East West Realty and RE/MAX New Horizons, both with agents experienced in vacation rental markets around the Chequamegon Bay area. Vacasa and RedAwning offer property management services for Airbnb investors in the region, while AirDNA provides market analytics specifically for short-term rental investments in northern Wisconsin markets. Roofstock and Mashvisor serve as national platforms helping investors identify profitable Airbnb properties, with Mashvisor offering specific rental yield calculations for Ashland's tourism market. Local property management companies like Northwoods Property Management and Superior Shores Property Services cater to vacation rental investors, while BiggerPockets connects investors with local real estate professionals familiar with Ashland's seasonal rental market driven by outdoor recreation and proximity to the Apostle Islands.