Is Oregon, Wisconsin Good for Airbnb Investment?

To start an Airbnb in Oregon, Wisconsin, begin by researching local zoning laws and regulations through the Oregon city clerk's office, as Wisconsin municipalities have varying short-term rental requirements that may include registration, licensing, and occupancy limits. Obtain necessary permits such as a business license from Oregon's city hall, register for Wisconsin state sales tax collection, and secure any required conditional use permits if operating in residential zones. Find a suitable property by analyzing local tourism demand, proximity to attractions like the Wisconsin River or local parks, and ensuring the property meets safety requirements including smoke detectors, carbon monoxide detectors, and adequate egress windows. Furnish the space with essential amenities including quality bedding, kitchen supplies, Wi-Fi, and local guidebooks while ensuring compliance with Wisconsin's landlord-tenant laws regarding furnished rentals. Create your Airbnb listing with professional photography, detailed descriptions highlighting nearby attractions, and competitive pricing based on comparable properties in the Oregon area. For ongoing management, establish cleaning protocols between guests, maintain responsive communication, collect and remit Wisconsin's 5.5% sales tax plus any local room taxes, keep detailed records for tax purposes, and consider obtaining short-term rental insurance since standard homeowner's policies typically exclude commercial activities. Additionally, familiarize yourself with Wisconsin's consumer protection laws and maintain compliance with any homeowner association rules if applicable.

For identifying profitable short-term rental properties in Oregon and Wisconsin, focus on locations within 30 minutes of major attractions like Crater Lake, Mount Hood, Wisconsin Dells, or Door County, prioritizing properties near ski resorts, lakes, or urban centers like Portland and Madison. Target 2-4 bedroom homes with unique features such as hot tubs, fireplaces, mountain or water views, and outdoor spaces, ensuring properties have strong WiFi infrastructure and are in neighborhoods with favorable STR regulations. Conduct pricing analysis using AirDNA and Mashvisor to identify markets with average daily rates above $150 and occupancy rates over 65%, while researching local competition density through Airbnb and VRBO searches to find areas with fewer than 20 listings per square mile. Utilize Oregon-specific resources like the Oregon Association of Realtors MLS data, local tourism boards such as Travel Oregon, and Wisconsin's Department of Tourism statistics, while leveraging tools like Rabbu, AllTheRooms, and local Facebook groups for market insights. Research municipal regulations in cities like Bend, Ashland, Lake Geneva, and Fish Creek, as these markets often have seasonal demand patterns with peak rates during summer months and winter ski seasons, making properties near year-round attractions particularly valuable for consistent cash flow.

To obtain an Airbnb/STR permit in Oregon, Wisconsin, you must first contact the Oregon Village Clerk's office at 608-835-3165 or visit the village hall at 118 Janesville Street to request a short-term rental application. Required documents 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 a $100 application fee payable to the Village of Oregon. The village requires properties to meet all building and fire codes, have working smoke and carbon monoxide detectors in each bedroom and common area, provide adequate parking (typically 2 spaces minimum), maintain occupancy limits based on square footage (generally 2 people per bedroom plus 2 additional), and display the permit number in all advertising. You must also register with the Wisconsin Department of Revenue for tax collection purposes and obtain a seller's permit if not already held. The approval process typically takes 30-45 days after submission of complete application materials, and annual renewal is required by December 31st each year with a $50 renewal fee. Properties are subject to inspection before initial approval and may be inspected annually thereafter, and operators must maintain a guest registry and respond to complaints within 2 hours during rental periods.

Short-term rentals (STRs) are legal in Oregon but subject to varying local regulations and state oversight. Oregon passed comprehensive STR legislation in 2021 (HB 2001) that allows local governments to regulate STRs while preventing outright bans, though cities can limit them in certain residential zones. Most Oregon cities including Portland, Bend, and Eugene have implemented registration requirements, occupancy limits, safety standards, and tax collection mandates. Portland requires STR permits and limits the number of non-hosted rentals, while coastal communities like Cannon Beach have stricter regulations due to housing shortage concerns. The state requires STR operators to collect transient lodging taxes, and many jurisdictions have implemented noise ordinances, parking requirements, and neighbor notification processes. Recent changes include increased enforcement mechanisms and standardized safety requirements across municipalities, with some cities like Bend implementing caps on STR permits in residential neighborhoods to address housing availability concerns.

The best Airbnb investment areas in Oregon include Portland's Pearl District and Hawthorne neighborhoods, which attract business travelers and urban tourists with their proximity to downtown attractions, restaurants, and cultural venues. Bend's Old Mill District and downtown area offer excellent returns due to year-round outdoor recreation tourism, skiing at Mount Bachelor, and summer festivals. The Oregon Coast towns of Cannon Beach and Newport provide strong seasonal rental income from beach tourism and storm watching. Hood River's downtown area capitalizes on windsurfing, kiteboarding, and Columbia River Gorge tourism. In Wisconsin, Milwaukee's Third Ward and Bay View neighborhoods attract business travelers to the city's corporate headquarters and tourists visiting breweries and lakefront attractions. Wisconsin Dells' downtown area remains highly profitable due to its status as a major family vacation destination with water parks and outdoor activities. Door County's Fish Creek and Ephraim areas command premium rates during summer months for their scenic lakefront locations and tourist attractions. Madison's State Street corridor and near-campus areas benefit from University of Wisconsin events, state government business travel, and cultural tourism, providing consistent year-round occupancy.

In Oregon, Airbnb hosts are subject to transient lodging taxes that vary by locality, with Portland charging 11.5% (including city and county portions), while other cities like Eugene charge around 9-12% depending on the specific municipality. Oregon requires hosts to register for a transient lodging tax license, collect taxes from guests, and remit payments monthly or quarterly depending on volume, with the state's central registration system allowing for streamlined compliance across multiple jurisdictions. In Wisconsin, short-term rental operators must collect the state's 5% sales tax plus local room taxes that range from 3-8% in major cities like Milwaukee (8.5% total) and Madison (approximately 8% total), with collection occurring through the state's My Tax Account system and remittance required monthly if collections exceed $300 annually. Both states generally exempt stays of 30 days or longer from transient occupancy taxes, and Wisconsin provides exemptions for certain non-profit organizations and government employees on official business, while Oregon offers similar exemptions for qualifying organizations and extended-stay arrangements, with platforms like Airbnb often facilitating automatic collection and remittance in participating jurisdictions since 2017-2019 through agreements with state and local tax authorities.

Starting an Airbnb in Oregon and Wisconsin involves significant upfront investments with notable regional differences. In Oregon, the median property purchase price is approximately $520,000 (2024), while Wisconsin offers more affordable options at around $280,000. Furnishing costs typically range from $15,000-25,000 for a complete 2-3 bedroom setup in both states, including furniture, appliances, linens, and decor. Initial setup expenses including professional photography, listing creation, and basic renovations average $3,000-5,000. Permits and fees vary significantly by municipality, with Oregon cities like Portland requiring business licenses and short-term rental permits totaling $500-2,000, while Wisconsin fees are generally lower at $200-800. Insurance costs run $1,500-3,000 annually for short-term rental coverage in both states. Utility setup and deposits average $500-1,000, with monthly costs of $200-400 depending on property size and season. First six months of operating costs including utilities, cleaning services, supplies, platform fees, and maintenance typically total $8,000-12,000. The total startup cost for Oregon ranges from $548,000-565,000, while Wisconsin presents a more accessible entry point at $308,000-325,000, making Wisconsin significantly more attractive for new investors seeking lower barriers to entry in the short-term rental market.

Airbnb properties in Oregon and Wisconsin show varying profitability depending on location and property type, with Oregon generally outperforming Wisconsin due to higher tourism demand. In Oregon, properties in Portland average $3,200-4,800 monthly revenue with 65-75% occupancy rates, while coastal properties like those in Cannon Beach can generate $4,000-7,000 monthly during peak seasons, though expenses including cleaning fees ($75-150 per turnover), property management (15-25% of revenue), utilities ($200-400 monthly), and insurance ($1,200-2,000 annually) typically consume 40-50% of gross revenue, resulting in profit margins of 25-35%. Wisconsin properties, particularly in Milwaukee and Madison, generate lower revenues of $2,000-3,500 monthly with 50-65% occupancy rates, while Wisconsin Dells vacation rentals can reach $3,500-5,500 during summer months, but similar expense ratios of 45-55% yield profit margins of 20-30%. Success factors include strategic location near attractions or business districts, professional photography, dynamic pricing strategies, and maintaining 4.8+ star ratings, with properties like a renovated 1920s bungalow in Portland's Hawthorne district reportedly generating $65,000 annually with $42,000 in expenses for a 35% profit margin, while a lakefront cabin in Wisconsin's Northwoods achieved $48,000 annual revenue with $31,000 expenses for a 35% margin despite lower occupancy due to premium pricing during peak fishing and fall foliage seasons.

Airbnb investments in Oregon and Wisconsin typically generate annual ROI of 8-15% and 6-12% respectively, with Oregon markets like Portland and coastal areas commanding higher returns due to tourism demand. Cash-on-cash returns in Oregon average 12-18% annually, while Wisconsin properties, particularly in Madison and Milwaukee, achieve 8-14% cash-on-cash returns. Oregon investments generally reach profitability within 18-24 months due to higher nightly rates ($120-250) and occupancy rates of 65-75%, while Wisconsin properties typically break even in 24-36 months with average nightly rates of $80-180 and occupancy rates of 55-70%. Coastal Oregon properties and ski resort areas can achieve ROI up to 20% annually, while Wisconsin lake properties and Door County locations perform similarly to Oregon's premium markets, with both states showing seasonal variations that impact overall profitability timelines.

STRSearch is a leading national platform that specializes in identifying profitable short-term rental properties across multiple markets including Oregon and Wisconsin. In Oregon, local services include Portland-based Vacasa which offers property management and acquisition consulting, Northwest Real Estate Capital focusing on investment properties in Portland and coastal markets, and Oregon Coast Vacation Rentals providing market analysis for coastal Airbnb investments. Wisconsin-specific services include Milwaukee's Brew City Properties specializing in urban short-term rental investments, Wisconsin Dells vacation rental specialists like Dells Vacation Rentals, and Lake Geneva-focused agents at Geneva Lake Realty who understand the seasonal rental market. National services operating in both states include Awning which provides comprehensive Airbnb investment analysis and property sourcing, Mashvisor offering data-driven investment property search tools, BiggerPockets marketplace connecting investors with local agents experienced in short-term rentals, Roofstock focusing on turnkey rental properties, and AirDNA providing market data and investment insights. Additional local Oregon resources include Bend's High Desert Realty for mountain market investments and Hood River vacation rental specialists, while Wisconsin investors can utilize Madison-area firms like First Weber Realty's investment division and Door County specialists at Door County Living who understand the tourism-driven rental market dynamics in these profitable Airbnb regions.