Is Lee, Massachusetts Good for Airbnb Investment?

To start an Airbnb in Lee, Massachusetts, begin by researching local zoning laws and regulations through the Lee Town Hall, as the Berkshire County town may have specific short-term rental ordinances that require registration or permits. Contact the Lee Building Department to determine if you need a business license or special use permit, and check with the Massachusetts Department of Revenue for state tax requirements including the 5.7% state sales tax and local option taxes. Find a suitable property by searching real estate listings in Lee's residential areas, ensuring the property is zoned for short-term rentals and considering proximity to popular Berkshire attractions like Tanglewood and local ski areas. Obtain necessary permits which may include a business certificate from the Lee Town Clerk, fire safety inspections, and potentially a Board of Health permit depending on the property type. Furnish the space with quality furniture, linens, kitchen essentials, and safety equipment including smoke detectors, carbon monoxide detectors, and fire extinguishers as required by Massachusetts fire codes. Create your Airbnb listing with professional photos highlighting Lee's scenic mountain location and proximity to cultural attractions, setting competitive rates based on seasonal demand in the Berkshires. Manage your property by establishing check-in procedures, maintaining cleanliness standards, responding promptly to guest communications, and keeping detailed records for tax purposes while ensuring compliance with Massachusetts short-term rental tax collection requirements and any local occupancy limits or noise ordinances specific to Lee.

To identify profitable short-term rental properties in Lee, Massachusetts, focus on locations within 2-3 miles of Tanglewood Music Center and near outdoor recreation areas like October Mountain State Forest, as these drive peak summer demand from music festival attendees and year-round visitors seeking Berkshire Mountains experiences. Target 2-4 bedroom properties built after 1950 with modern amenities, full kitchens, outdoor spaces, and parking, as these command $150-300 per night during peak season (June-September) versus $80-150 in off-season. Analyze comparable STR properties using AirDNA and Mashvisor to benchmark occupancy rates of 60-75% annually, with successful properties generating $35,000-65,000 gross revenue depending on size and location. Research competition by monitoring active Airbnb and VRBO listings within 5 miles, noting that properties closer to Tanglewood and with unique features like hot tubs or mountain views achieve premium pricing. Utilize tools like Rabbu and STR Helper for Lee-specific market analysis, check local zoning regulations through Lee's Planning Board since some residential areas restrict STRs, and consider properties near Route 20 corridor for easy access while maintaining the rural Berkshires appeal that attracts visitors seeking authentic New England experiences.

To obtain an Airbnb/STR permit in Lee, Massachusetts, you must first contact the Lee Building Department at Town Hall located at 32 Main Street to inquire about short-term rental registration requirements, as Massachusetts General Law Chapter 64G requires host registration with the state. Submit an application to the Massachusetts Department of Revenue for a short-term rental registration certificate, providing your property address, contact information, tax identification number, and proof of liability insurance coverage of at least $1 million. Required documents typically include a completed state registration form, proof of property ownership or lease agreement, certificate of liability insurance, floor plan showing maximum occupancy, and payment of the $200 annual state registration fee. At the local level, contact Lee's Planning Board or Zoning Department to ensure your property complies with local zoning ordinances and obtain any required local permits, which may require additional documentation such as a site plan, parking verification, and septic system compliance if applicable. The state registration process typically takes 2-4 weeks once all documents are submitted, while local permitting timelines vary but generally require 30-60 days depending on Lee's specific review process. You must also register for Massachusetts sales tax collection and remittance, display your registration number in all listings, and ensure compliance with local noise ordinances, parking requirements, and occupancy limits as determined by Lee's zoning bylaws and building codes.

Short-term rentals (STRs) are legal in Lee, Massachusetts, but operate under state regulations and local oversight. Massachusetts allows STRs statewide with required registration through the state's Department of Revenue, mandatory liability insurance, and compliance with health and safety standards including smoke and carbon monoxide detectors. Lee, as a small Berkshire County town, generally permits STRs in residential areas but may have local zoning restrictions or permit requirements that property owners must follow. The state implemented comprehensive STR regulations around 2019 requiring operators to register annually, collect and remit state and local taxes, and maintain proper insurance coverage. While Lee doesn't appear to have enacted specific STR prohibitions like some larger Massachusetts municipalities, property owners must still comply with local building codes, occupancy limits, and any homeowners association restrictions. Recent changes have focused on tax compliance and safety requirements rather than outright bans, making Lee relatively STR-friendly compared to cities like Boston or Cambridge which have implemented stricter limitations on non-owner-occupied rentals.

The best areas for Airbnb investment in Lee, Massachusetts are downtown Lee near the historic Main Street district, which attracts visitors year-round due to its proximity to Tanglewood (summer home of the Boston Symphony Orchestra just 10 minutes away in Lenox), the Norman Rockwell Museum, and numerous Berkshire cultural attractions. The area near October Mountain State Forest offers excellent potential for nature tourism and outdoor recreation enthusiasts visiting for hiking, camping, and fall foliage viewing. Properties near Lee Premium Outlets provide strong appeal for shopping tourists and weekend visitors from New York and Boston metropolitan areas. The neighborhoods around Lee's antique shops and historic sites along Route 20 capture heritage tourism traffic, while areas with easy access to Mass Pike (I-90) are ideal for business travelers and those attending events at nearby venues like Berkshire Theatre Group in Stockbridge or Shakespeare & Company in Lenox. The residential areas near Lee Middle and High School can serve families visiting for school events or relocating to the area, and properties within walking distance of local restaurants and cafes on Main Street maximize guest convenience and repeat bookings.

In Lee, Massachusetts, Airbnb hosts are subject to multiple lodging taxes including the state excise tax of 5.7% on short-term rentals under 31 days, plus the state sales tax of 6.25% on the total rental amount. Additionally, Berkshire County imposes a local option excise tax of 6% on short-term rentals, and the Town of Lee may collect a local rooms tax of up to 6% (estimated at 4-6% based on typical municipal rates in the region). These taxes are typically collected by Airbnb directly from guests at the time of booking for properties listed on their platform, with Airbnb remitting payments monthly to the Massachusetts Department of Revenue and local tax authorities. Hosts renting through other platforms or direct bookings must register with the state, collect taxes from guests, and remit payments quarterly using Form ST-9 for state taxes and appropriate local forms for municipal taxes. Exemptions generally apply to rentals of 31 days or longer, which are considered long-term stays rather than short-term rentals, and properties rented for fewer than 14 days per year may qualify for certain exemptions under federal tax rules, though state and local taxes may still apply.

To start an Airbnb in Lee, Massachusetts, expect total costs around $385,000-$425,000. Property purchase represents the largest expense at approximately $350,000 based on median home prices in the Berkshires region as of 2023. Furnishing costs typically range $15,000-$25,000 for a complete 2-3 bedroom property including beds, linens, kitchen essentials, and living room furniture from retailers like IKEA, Wayfair, and local suppliers. Initial setup costs including professional photography, listing creation, and basic renovations average $3,000-$5,000. Permits and fees in Massachusetts include short-term rental registration ($200-$500), potential local licensing fees ($100-$300), and tax registration which varies by municipality. Insurance costs approximately $1,500-$2,500 annually for short-term rental coverage through companies like Proper Insurance or CBIZ. Utility setup and deposits for electricity, gas, water, internet, and cable total around $500-$800 initially, with monthly costs of $200-$400. First six months operating expenses including utilities ($1,200-$2,400), cleaning supplies and services ($600-$1,200), maintenance reserves ($1,000), marketing ($300-$600), and platform fees to Airbnb typically total $4,000-$7,000, bringing the complete startup investment to approximately $385,000-$425,000 depending on property condition and furnishing choices.

Airbnb properties in Lee, Massachusetts, located in the scenic Berkshires region, typically generate annual revenues ranging from $15,000-$35,000 for seasonal properties, with peak summer months (June-September) accounting for 60-70% of bookings due to proximity to Tanglewood Music Center and fall foliage tourism. Operating expenses generally include 25-30% for cleaning and maintenance, 3% Airbnb service fees, 8-12% for utilities, and $2,000-$4,000 annually for property taxes, resulting in net profit margins of 35-45% for well-managed properties. Success factors include proximity to cultural attractions like Jacob's Pillow Dance Festival, offering amenities like hot tubs or fire pits, maintaining 4.8+ star ratings, and strategic pricing that averages $180-$250 per night during peak season versus $90-$140 in off-season. Properties within 10 miles of Lenox and Stockbridge command premium rates, with some luxury cabins near October Mountain State Forest achieving occupancy rates of 75-80% and generating $40,000+ annually, while basic properties further from attractions may struggle with 45-55% occupancy and $12,000-$18,000 annual revenues, making location and property differentiation critical for profitability in this competitive vacation rental market.

Airbnb investments in Lee, Massachusetts typically generate annual ROI of 8-12% with cash-on-cash returns ranging from 6-10%, primarily driven by the town's proximity to popular Berkshire attractions like Tanglewood and seasonal tourism demand. Properties in Lee generally achieve profitability within 18-24 months, with average daily rates of $150-220 during peak summer and fall foliage seasons, though occupancy rates fluctuate significantly between 65-75% in high season and 25-35% during winter months. The market benefits from Lee's location along Route 20 and accessibility to both outdoor recreation and cultural venues, with investors typically seeing stronger performance in properties that accommodate 4-8 guests and offer amenities like hot tubs or proximity to hiking trails, while the relatively affordable property acquisition costs compared to nearby Lenox or Stockbridge help improve overall investment returns.

STRSearch is a leading national platform that specializes in identifying profitable short-term rental properties for investors in Lee, Massachusetts and throughout the Berkshires region. Local real estate agents like Berkshire Property Agents and Guido & Associates have extensive experience with vacation rental properties in the Lee area, particularly around popular attractions like Tanglewood and October Mountain State Park. National services including AirDNA, Mashvisor, and BiggerPockets provide market analysis and property identification tools for Airbnb investments in the Berkshires. Regional specialists such as Berkshire Vacation Rentals and New England Short Term Rental Advisors offer consulting services for investors looking to enter the Lee market, which has seen strong demand due to its proximity to cultural attractions and outdoor recreation. Companies like RedAwning and Vacasa also provide property management services that can help investors maximize returns on Airbnb properties in Lee, while platforms such as RentSpree and Awning connect investors with turnkey short-term rental opportunities in Western Massachusetts markets including Lee and surrounding towns like Lenox and Stockbridge.