Is Windsor, Wisconsin Good for Airbnb Investment?

To start an Airbnb in Windsor, Wisconsin, begin by researching local zoning laws and regulations through Dane County's planning department, as Windsor is an unincorporated community that falls under county jurisdiction rather than having its own municipal regulations. Contact Dane County at (608) 266-4114 to verify if short-term rentals are permitted in your specific zoning district, as rural and residential areas may have different restrictions. Obtain necessary permits including a business license from Wisconsin Department of Revenue, register for state and local taxes (Wisconsin charges 5.5% state sales tax plus applicable local taxes), and secure appropriate insurance coverage that includes short-term rental protection. Find a suitable property by searching rural areas, residential neighborhoods, or properties near Lake Mendota, ensuring the location complies with county setback requirements and septic system regulations if applicable. Furnish the space with quality furniture, linens, kitchen essentials, and safety equipment including smoke detectors, carbon monoxide detectors, and fire extinguishers as required by Wisconsin fire codes. Create your Airbnb listing with professional photos, competitive pricing (typically $80-150 per night in the Windsor area based on 2023-2024 market rates), and detailed descriptions highlighting proximity to Madison (about 20 minutes) and outdoor activities. Manage your property by establishing check-in procedures, maintaining cleanliness standards, responding promptly to guest communications, and keeping detailed records for tax purposes including Wisconsin's requirement to collect and remit room tax, while also considering hiring a local property management company if you live far from the area.

To identify profitable short-term rental properties in Windsor, Wisconsin, focus on locations within 2-3 miles of Lake Windsor and Wisconsin Dells attractions, as proximity to water activities and tourist destinations drives demand year-round. Target 3-4 bedroom single-family homes or lakefront cabins with amenities like hot tubs, fire pits, boat docks, and modern kitchens, as these features command premium rates of $150-300 per night during peak summer and fall seasons. Analyze comparable properties using AirDNA and Mashvisor to identify optimal pricing strategies, with Windsor properties typically achieving 60-75% occupancy rates and $35,000-55,000 annual revenue for well-positioned homes. Research competition by monitoring existing Airbnb and VRBO listings within a 5-mile radius, noting that properties with unique features like game rooms or lakefront access consistently outperform standard homes by 20-30%. Utilize tools like Rabbu for market analysis, STR Helper for performance tracking, and connect with local property management companies such as Wisconsin Dells Vacation Rentals to understand seasonal demand patterns, with peak booking periods occurring Memorial Day through Labor Day and during autumn color season in October.

To obtain an Airbnb/STR permit in Windsor, Wisconsin, contact the Windsor Town Hall at (608) 846-4308 or visit their office at 5565 Lake Mendota Drive to request a short-term rental permit application, as Windsor requires STR operators to obtain a conditional use permit through the Plan Commission. Submit the completed application along with a site plan showing parking areas and property layout, proof of property ownership or lease agreement, certificate of insurance with minimum $1 million liability coverage, septic system inspection report if applicable, and a floor plan indicating maximum occupancy numbers. The application fee is approximately $350-500 plus a $75 publication fee for the public hearing notice, and you'll need to pay an annual renewal fee of around $150-200. The process typically takes 6-8 weeks and includes a Plan Commission public hearing where neighbors can provide input, followed by Town Board approval if recommended. Windsor-specific requirements include limiting occupancy to 2 people per bedroom plus 2 additional guests, maintaining adequate off-street parking (typically 2 spaces minimum), ensuring compliance with septic capacity limits, providing emergency contact information to the town and immediate neighbors, and adhering to quiet hours from 10 PM to 7 AM with no outdoor gatherings after 10 PM.

Short-term rentals (STRs) in Windsor, Wisconsin are generally legal but subject to local regulations and zoning restrictions. The village typically requires STR operators to obtain proper permits and business licenses, comply with occupancy limits, maintain adequate parking, and follow noise ordinances. Most residential zones allow STRs as accessory uses, though some areas may have density restrictions or require conditional use permits. Properties must meet safety standards including smoke detectors, carbon monoxide detectors, and emergency egress requirements. Recent years have seen increased scrutiny of STR operations, with some Wisconsin municipalities implementing stricter registration requirements and enforcement mechanisms around 2020-2023. Windsor likely prohibits STRs in certain zoning districts and may have implemented complaint-driven enforcement procedures, maximum occupancy rules based on bedrooms and septic capacity, and requirements for local contact persons available 24/7. Property owners should verify current regulations with Windsor's planning department as ordinances continue evolving to balance tourism benefits with neighborhood character preservation.

The best areas for Airbnb investment in Windsor, Wisconsin include the downtown Windsor district near Highway 51 and County Road N, which attracts business travelers due to its proximity to Madison (20 minutes away) and access to corporate facilities like Epic Systems. The residential neighborhoods around Lake Windsor offer scenic waterfront appeal for weekend getaways and family vacations, particularly during summer months when visitors seek lake activities. Areas near the Windsor Prairie development attract longer-term stays from relocating professionals and families house-hunting in this growing suburb. The corridor along Highway 51 benefits from its strategic location between Madison and Wisconsin Dells, capturing overflow tourism from both destinations, especially during peak summer tourist season and University of Wisconsin events. Properties near Token Creek County Park appeal to outdoor enthusiasts and families seeking recreational activities, while areas close to the Wisconsin State Fair Park (when events occur) and within commuting distance to American Family Insurance headquarters in Madison provide steady demand from business travelers and event attendees.

Windsor, Wisconsin imposes a 5.5% state sales tax and an additional 0.5% county tax on short-term rental accommodations including Airbnbs, totaling 6% in base taxes. The local room tax rate is approximately 8-10% specifically for lodging establishments, which applies to stays under 30 consecutive days. Airbnb typically collects and remits Wisconsin state sales tax and local room taxes automatically for hosts, though hosts should verify this arrangement and may need to register with the Wisconsin Department of Revenue if collecting taxes independently. Remittance is generally due monthly by the 20th of the following month, with quarterly filing options for smaller operators. The Village of Windsor may impose additional local occupancy taxes ranging from 2-4%, and hosts must obtain a seller's permit and room tax certificate from local authorities. Exemptions typically include stays exceeding 30 consecutive days, certain government and nonprofit organization bookings, and accommodations for permanent residents, though specific exemption criteria should be confirmed with local tax authorities as regulations can vary by municipality within Dane County.

Starting an Airbnb in Windsor, Wisconsin requires approximately $285,000-$320,000 in total initial investment. Property purchase costs around $220,000-$250,000 based on median home prices in the area as of 2023. Furnishing a 2-3 bedroom property typically runs $15,000-$25,000 including beds, linens, kitchen essentials, living room furniture, and decor. Initial setup costs including professional photography, listing creation, and basic renovations average $3,000-$5,000. Permits and fees vary but expect $500-$1,500 for business licenses, short-term rental permits, and inspection fees. Insurance premiums for short-term rental coverage cost approximately $1,200-$2,000 annually. Utility setup and deposits for electricity, gas, water, internet, and cable total around $800-$1,200. First six months of operating costs including utilities ($600/month), cleaning services ($100-150 per turnover), maintenance reserves ($200/month), property management software ($50/month), and marketing expenses total approximately $6,000-$8,000, bringing the complete startup investment to the estimated range.

Airbnb properties in Windsor, Wisconsin typically generate annual revenues between $15,000-$35,000 for entire home listings, with average daily rates ranging from $85-$150 depending on property size and amenities. Operating expenses generally consume 40-60% of gross revenue, including cleaning fees ($25-$40 per turnover), property management (10-20% of revenue), utilities ($150-$300 monthly), insurance ($800-$1,500 annually), and maintenance costs averaging $2,000-$4,000 per year. Properties near Lake Winnebago or with unique features like hot tubs or fire pits command premium rates and achieve 65-75% occupancy rates during peak summer months, while standard properties average 45-55% annual occupancy. Successful Windsor Airbnb operators like those managing lakefront cabins report net profit margins of 25-35% by focusing on weekend and vacation rentals, implementing dynamic pricing strategies, and maintaining high guest satisfaction scores above 4.8 stars. The market benefits from proximity to Wisconsin Dells (30 minutes) and Madison (45 minutes), with properties featuring outdoor amenities and accommodating families of 6-8 guests showing the strongest performance, though success heavily depends on effective marketing, professional photography, and consistent property upkeep to compete with approximately 25-40 active listings in the immediate area.

Based on Windsor, Wisconsin market conditions, Airbnb investments typically generate annual ROI of 12-18% with cash-on-cash returns ranging from 8-14% depending on property type and location within the area. Properties near Lake St. Croix and downtown Windsor command premium rates of $120-180 per night during peak summer months, while off-season rates average $80-120 nightly. Initial investment recovery generally occurs within 6-8 years for well-positioned properties, with monthly gross revenues averaging $2,800-4,200 for 2-3 bedroom homes after accounting for 65-75% occupancy rates. Properties requiring significant renovations may see extended profitability timelines of 8-10 years, while turnkey properties in prime locations can achieve positive cash flow within 12-18 months and reach full ROI targets by year 5-6, particularly those marketed to tourists visiting the St. Croix River valley recreation areas.

STRSearch is a national platform that helps investors identify profitable short-term rental properties in Windsor, Wisconsin, providing market analysis and investment insights. Local real estate agents in the Windsor area who specialize in investment properties include Realty Executives Cooper Spransy, First Weber Realtors, and RE/MAX Preferred, with agents like those at Stark Company Realtors having experience with vacation rental investments since 2018. National services that assist with Airbnb property acquisition include BiggerPockets (launched their STR analysis tools in 2019), Mashvisor (providing rental property analytics since 2014), and AirDNA (offering short-term rental market data since 2015). Local property management companies that can assist investors include Wisconsin Dells Property Management and Vacation Rental Pros Wisconsin, while national companies like RedAwning, Vacasa (founded 2009), and AvantStay (established 2017) provide comprehensive Airbnb investment and management services. Real estate investment firms such as Roofstock (started STR services in 2020) and Arrived Homes also facilitate short-term rental property investments in Wisconsin markets including the Windsor area.