Is Windham, New York Good for Airbnb Investment?

To start an Airbnb in Windham, New York, begin by researching local zoning laws and regulations through the Town of Windham Planning Board, as the town requires short-term rental permits and compliance with residential zoning restrictions that typically limit rentals to no more than 14 consecutive days. Obtain necessary permits including a short-term rental license from the town clerk's office (approximately $100-200 annually), ensure your property meets fire safety codes with proper smoke detectors and carbon monoxide alarms, and register for New York State sales tax collection since you'll need to charge the 8% state sales tax plus Greene County's 3% occupancy tax. Find a suitable property by focusing on areas near Windham Mountain ski resort or scenic locations that attract tourists, ensuring the property allows short-term rentals in the deed restrictions and homeowners association rules if applicable. Furnish the space with durable, comfortable furniture emphasizing the mountain/outdoor theme popular in the Catskills region, including essential amenities like high-speed internet, heating systems capable of handling winter temperatures, and outdoor equipment storage for ski and hiking gear. List your property on Airbnb with professional photos highlighting mountain views and proximity to outdoor activities, setting competitive rates based on seasonal demand (higher during ski season December-March and summer months June-August, typically $150-300 per night for a 2-bedroom unit). Manage the property by establishing relationships with local cleaning services, maintenance contractors familiar with mountain properties, and consider using property management companies like Catskills Property Management or local services that specialize in short-term rentals in the Greene County area, while maintaining responsive communication with guests and ensuring compliance with the town's noise ordinances and parking restrictions.

To identify profitable short-term rental properties in Windham, New York, focus on locations within 2-3 miles of Windham Mountain ski resort, Hunter Mountain (15 minutes away), and scenic areas along Route 23 and Route 296 with mountain or valley views. Target 3-4 bedroom properties built after 1980 with modern amenities, hot tubs, fireplaces, game rooms, and outdoor spaces that can accommodate 6-10 guests, as these command premium rates of $200-400 per night during peak ski season (December-March) and summer months (June-August). Analyze comparable properties on Airbnb and VRBO within a 5-mile radius, noting that successful properties typically achieve 60-70% occupancy rates with average daily rates dropping to $150-250 during shoulder seasons. Research competition by monitoring listings from companies like Vacasa, RedAwning, and local property management firms, while identifying gaps in luxury amenities or unique property features. Utilize tools like AirDNA, Mashvisor, and Rabbu for market analysis, examine Windham's tourism data through Greene County tourism boards, and leverage local real estate platforms like MLS and LoopNet, while connecting with Windham-area realtors who specialize in vacation properties and understand seasonal rental regulations and tax implications specific to Greene County.

To obtain an Airbnb/STR permit in Windham, New York, you must first contact the Windham Town Clerk's office at the Town Hall located at 5521 State Route 23, Windham, NY 12496, as the town requires short-term rental registration under local zoning ordinances. Submit a completed short-term rental application form along with a copy of your property deed, certificate of occupancy, proof of liability insurance (minimum $1 million coverage), floor plan showing maximum occupancy, septic system inspection certificate if applicable, and a $150 application fee plus $75 annual renewal fee. Required documents also include a fire safety inspection report, carbon monoxide and smoke detector certification, emergency contact information for a local representative within 30 minutes of the property, and parking plan showing adequate off-street parking. Windham specifically requires STR properties to maintain a maximum occupancy of 2 people per bedroom plus 2 additional guests, quiet hours from 10 PM to 8 AM, and compliance with the town's noise ordinance. The application process typically takes 4-6 weeks for review and approval, during which time the building inspector will conduct a property inspection to ensure compliance with fire safety codes and zoning requirements. Once approved, you must display the permit number in all online listings and renew annually by December 31st with updated insurance documentation and any required re-inspections.

Short-term rentals (STRs) are generally legal in Windham, New York, but operate under Greene County regulations and New York State laws that require hosts to register with the state and collect occupancy taxes. The town of Windham, located in the Catskills region, has seen increased STR activity since around 2015-2020, particularly through platforms like Airbnb and VRBO, as the area attracts tourists for skiing, hiking, and outdoor recreation. While there are no blanket prohibitions on STRs in Windham, properties must comply with local zoning ordinances, building codes, and safety requirements including smoke and carbon monoxide detectors. Some residential neighborhoods may have deed restrictions or HOA rules limiting short-term rentals, and hosts must obtain proper permits and pay local occupancy taxes. Recent changes include New York State's 2021 requirement for STR registration and tax collection, while Greene County has considered additional regulations around noise, parking, and occupancy limits. Properties in certain historic districts or environmentally sensitive areas near the Catskill Park may face additional restrictions, and hosts should verify compliance with both town zoning laws and any applicable homeowners association rules before operating an STR.

The best areas for Airbnb investment in Windham, New York include the Village of Windham center, which attracts year-round visitors due to its proximity to Windham Mountain Resort and serves as a hub for skiing in winter and hiking/mountain biking in summer. The Windham Path area near Route 296 is highly desirable for its easy access to both the ski slopes and the scenic Windham Path rail-trail, drawing outdoor enthusiasts and families seeking recreational activities. Properties near Windham Country Club appeal to golf tourists and wedding parties, as the club hosts numerous events throughout the warmer months. The South Street and Mitchell Hollow Road corridors offer attractive investment opportunities due to their balance of privacy and accessibility, appealing to city dwellers from New York City and Albany seeking weekend retreats in the Catskills. The area around Windham Civic Association and near the town's antique shops and restaurants benefits from cultural tourism and leaf-peeping visitors during fall foliage season, while properties with mountain views or near hiking trail access points command premium rates from nature tourists and photographers visiting this part of Greene County's Catskill Mountains region.

In Windham, New York, Airbnb hosts are subject to New York State sales tax of 8% on lodging rentals, plus Greene County's local occupancy tax of 3%, for a combined rate of 11% on short-term rental income. The state sales tax applies to rentals of less than 90 days and is collected either directly by Airbnb through their automatic tax collection service for participating jurisdictions or must be collected by hosts and remitted quarterly to the New York State Department of Taxation and Finance using form ST-809. Greene County's occupancy tax must be collected by hosts and remitted monthly to the Greene County Treasurer's office, typically due by the 20th of the following month. Hosts earning over $20,000 annually or conducting more than 200 transactions must register for sales tax permits with New York State. Exemptions may apply for rentals to permanent residents (90+ days), certain government employees on official business, and stays paid for by exempt organizations, though documentation is required. Additionally, hosts may need to comply with local licensing requirements and should verify current rates and procedures with both state and county tax authorities as regulations can change.

Starting an Airbnb in Windham, New York requires approximately $350,000-$450,000 in total initial investment. Property purchase costs average $280,000-$350,000 for a median 2-3 bedroom home suitable for short-term rentals in this Catskills region. Furnishing costs range $15,000-$25,000 including beds, linens, kitchen essentials, living room furniture, and outdoor equipment for seasonal activities. Initial setup expenses total $3,000-$5,000 covering professional photography, listing optimization, welcome materials, and basic technology like smart locks and WiFi upgrades. Permits and fees include a $200-$500 short-term rental permit from Greene County, $300-$800 in business registration and tax setup, and potential HOA approval costs of $100-$300. Insurance premiums for short-term rental coverage cost $2,000-$3,500 annually. Utility setup and deposits require $500-$1,000 initially, with monthly costs of $200-$400 for electricity, heating, water, internet, and cable. First six months operating costs total $8,000-$12,000 including utilities ($1,200-$2,400), cleaning services ($1,800-$3,000), maintenance and supplies ($1,500-$2,500), marketing and platform fees ($2,000-$3,000), and property management software ($300-$600). Additional working capital of $5,000-$10,000 is recommended for unexpected repairs and seasonal fluctuations in this mountain resort area.

Airbnb properties in Windham, New York, particularly those near ski resorts like Windham Mountain, typically generate strong seasonal profitability with average daily rates ranging from $150-300 during peak winter months (December-March) and $100-200 during summer season. A typical 3-bedroom property can gross $35,000-55,000 annually, with expenses including mortgage payments ($1,500-2,500/month), property management fees (15-25% of revenue), cleaning costs ($75-125 per turnover), utilities ($200-400/month), insurance ($2,000-3,500/year), and maintenance ($3,000-6,000/year), resulting in net profit margins of 20-35% for well-managed properties. Success factors include proximity to Windham Mountain Resort (properties within 2 miles command premium rates), ski-in/ski-out access, hot tubs, fireplaces, and accommodating 6-12 guests. Case studies from 2022-2023 show that a 4-bedroom chalet near the base lodge achieved 65% occupancy with $48,000 gross revenue and $31,000 net profit, while a smaller 2-bedroom property averaged $28,000 gross with $18,000 net profit. Properties managed by companies like Vacasa or RedAwning typically see higher occupancy rates (55-70%) compared to self-managed units (40-55%), though management fees reduce overall margins by 10-15 percentage points.

Airbnb investments in Windham, New York typically generate annual ROI of 12-18% due to the area's proximity to ski resorts like Windham Mountain and Hunter Mountain, with peak winter season bookings driving higher returns. Cash-on-cash returns generally range from 8-14% annually, depending on property acquisition costs and financing structure, with properties averaging $300-500 per night during ski season (December-March) and $150-250 during summer months. Most investors achieve profitability within 18-24 months, particularly for properties purchased in the $400,000-600,000 range with 20-25% down payments, as the Catskills region has seen consistent vacation rental demand growth of approximately 15-20% annually since 2019, driven by New York City residents seeking weekend retreats within a 2-3 hour drive.

STRSearch is a leading national platform that specializes in identifying profitable short-term rental properties for investors, including in Windham, New York. Local real estate agents in the Catskills region such as Coldwell Banker Village Green Realty, Keller Williams Hudson Valley, and Century 21 New West Properties have experience with vacation rental investments in Windham and surrounding areas. National services like AirDNA provide market analytics and property performance data for the Windham market, while Mashvisor offers investment property analysis tools specifically for Airbnb properties. RedAwning and Vacasa provide property management services that can help investors identify and manage profitable properties in the area. Local property management companies such as Catskill Mountains Vacation Rentals and Mountain Top Property Management offer specialized knowledge of the Windham market and can assist with both acquisition and management of Airbnb properties. Additionally, platforms like Roofstock and BiggerPockets connect investors with turnkey rental properties and investment opportunities, though their Windham-specific inventory may be limited given the smaller market size.