Is Monterey, Massachusetts Good for Airbnb Investment?

To start an Airbnb in Monterey, Massachusetts, begin by researching local zoning laws and regulations through the Monterey Town Hall, as this small Berkshire County town may have specific short-term rental ordinances that require registration or permits. Contact the Monterey Building Inspector and Board of Health to determine if you need a lodging license, occupancy permit, or health department approval, which typically costs $50-200 annually. Find a suitable property by searching local real estate listings or consider converting existing residential space, ensuring it meets safety requirements including smoke detectors, carbon monoxide detectors, and proper egress routes. Furnish the space with quality basics including comfortable bedding, towels, kitchen essentials, WiFi, and local guidebooks highlighting nearby attractions like Beartown State Forest and Tanglewood. Create your Airbnb listing with professional photos, competitive pricing around $100-250 per night depending on season and amenities, and highlight Monterey's proximity to Great Barrington and outdoor activities. Obtain proper insurance coverage through your homeowner's policy or Airbnb's Host Protection Insurance, collect and remit Massachusetts state taxes (5.7% sales tax plus local occupancy taxes), and establish a management system for guest communication, cleaning between stays, and property maintenance to ensure positive reviews and repeat bookings.

To identify profitable short-term rental properties in Monterey, Massachusetts, focus on properties within 2-3 miles of popular attractions like Beartown State Forest and close to major routes connecting to the Berkshires tourism corridor, as location proximity to outdoor recreation and cultural sites drives 60-70% higher occupancy rates. Target 2-4 bedroom properties built after 1980 with modern amenities, full kitchens, outdoor spaces, and parking, as these command $150-250 per night versus $80-120 for basic accommodations. Conduct pricing analysis using AirDNA and Mashvisor to benchmark against similar properties in nearby Great Barrington and Lee, aiming for properties that can achieve 65%+ annual occupancy with average daily rates of $180-220. Research competition within a 10-mile radius using Airbnb and VRBO searches, identifying gaps in luxury or pet-friendly offerings that typically see 15-20% premium pricing. Utilize tools like STR Helper for Monterey-specific regulations, Rabbu for market analysis, and connect with Berkshire County tourism boards for seasonal demand patterns, while partnering with local property management companies like Berkshire Property Agents who understand the seasonal influx from Boston and New York markets that peaks during fall foliage season generating 40-50% of annual revenue.

To obtain an Airbnb/STR permit in Monterey, Massachusetts, you must first contact the Monterey Town Clerk's office at Town Hall located at 435 Main Road to inquire about local short-term rental regulations, as this small Berkshire County town may have specific bylaws governing STRs that were likely enacted around 2019-2021 following statewide legislation. You'll need to submit an application that typically requires a completed STR registration form, proof of property ownership or lease agreement, floor plan of the rental unit, proof of liability insurance (minimum $1 million), contact information for a local representative available 24/7, and a copy of your state tax registration. The application fee is estimated at $200-400 annually, and you must also register with the Massachusetts Department of Revenue for state tax purposes and obtain a Certificate of Registration, which costs approximately $50. Required documents include a septic system inspection certificate if applicable, fire safety compliance documentation, and parking plan showing adequate off-street parking spaces. The approval timeline is typically 30-60 days after submitting a complete application, and Monterey likely requires STRs to maintain occupancy limits based on septic capacity, provide adequate parking, ensure quiet hours compliance, and may restrict the total number of rental days per year to 185 days or require owner occupancy for certain property types, with annual renewal required and potential inspections by local officials.

Short-term rentals (STRs) are legal in Monterey, Massachusetts, but operate under state regulations and local oversight. Massachusetts allows STRs statewide under legislation passed in 2018-2019, requiring operators to register with the state, collect occupancy taxes, and maintain liability insurance. In Monterey, a small Berkshire County town, STRs must comply with state requirements including a 5.7% state excise tax plus local option taxes if adopted by the town. The town has authority to implement additional local regulations such as safety inspections, noise ordinances, and parking requirements, though specific local restrictions vary by municipality. Properties in residential zones are generally permitted for STR use unless specifically prohibited by local zoning bylaws. Recent changes include enhanced tax collection mechanisms and improved registration systems implemented around 2019-2020. Operators must register annually with the Massachusetts Department of Revenue and may need local permits depending on Monterey's specific ordinances, which typically address issues like occupancy limits, safety standards, and neighbor notification requirements.

The best areas for Airbnb investment in Monterey, Massachusetts include the Historic Downtown District near the town center, which attracts visitors interested in colonial architecture and local festivals throughout the year, particularly during fall foliage season from September to November. The Berkshire Hills vicinity offers strong potential due to proximity to outdoor recreation activities like hiking and skiing, drawing tourists year-round to nearby state parks and seasonal attractions. The Main Street corridor provides excellent investment opportunities given its walkability to local restaurants, antique shops, and the annual Monterey General Store events that bring consistent foot traffic. Properties near Lake Garfield and Benedict Pond are highly desirable for summer vacation rentals, attracting families and outdoor enthusiasts from Boston and New York metropolitan areas seeking weekend getaways. The Route 23 corridor offers good accessibility for business travelers and tourists heading to nearby Tanglewood Music Center in Lenox and other Berkshire County attractions, making it a strategic location for year-round bookings with peak seasons during summer music festivals and winter ski season.

Airbnb properties in Monterey, Massachusetts are subject to the state's 5.7% short-term rental excise tax, which applies to rentals of 31 days or less, collected by platforms like Airbnb and remitted quarterly to the Massachusetts Department of Revenue. Additionally, hosts must pay the state's 6.25% sales tax on short-term rentals, though this is also typically collected by Airbnb and other platforms automatically. At the local level, Monterey may impose a local option excise tax of up to 6% on short-term rentals, which would be collected alongside the state taxes and remitted to the town, though the specific rate varies by municipality and some towns opt not to impose this tax. The regular state hotel tax of 5.7% also applies to these rentals. Hosts operating through platforms generally don't need to manually remit these taxes as they're collected at booking, but those renting directly to guests must register with the state, collect applicable taxes, and file quarterly returns. Exemptions typically include rentals of 31 days or longer, and some municipalities may exempt certain types of properties or operators below specific revenue thresholds.

To start an Airbnb in Monterey, Massachusetts, the total costs would be approximately $485,000-$565,000. Property purchase represents the largest expense at $400,000-$450,000 based on median home prices in the Berkshire County area where Monterey is located. Furnishing costs typically range $15,000-$25,000 for a complete setup including beds, linens, kitchen essentials, living room furniture, and décor to create an appealing guest experience. Initial setup costs including professional photography, listing creation, welcome materials, and basic supplies total around $2,000-$3,000. Permits and fees vary but generally include short-term rental permits ($200-$500), business registration ($100-$300), and potential zoning compliance costs ($500-$1,500). Insurance for short-term rentals runs $1,500-$3,000 annually, significantly higher than standard homeowner's insurance. Utilities including electricity, water, heating, internet, and cable average $300-$500 monthly depending on property size and season. First six months of operating costs encompass utilities ($1,800-$3,000), cleaning services between guests ($150-$250 per turnover), maintenance and repairs ($2,000-$4,000), marketing and platform fees to Airbnb and VRBO (3-5% of bookings), property management if outsourced ($3,000-$6,000), and miscellaneous supplies and amenities ($1,000-$2,000), totaling approximately $8,000-$15,000 for the initial six-month period.

Airbnb properties in Monterey, Massachusetts typically generate annual revenues between $15,000-$35,000 for seasonal rentals, with peak summer months (June-August) commanding $150-$300 per night depending on proximity to beaches and local attractions. Operating expenses generally range from $8,000-$18,000 annually, including property management fees (15-25%), cleaning costs ($75-$125 per turnover), utilities ($2,400-$3,600), insurance ($1,200-$2,000), and maintenance ($1,500-$3,000). Profit margins typically fall between 25-45%, with waterfront properties and those near popular destinations like Berkshire attractions achieving higher margins. Success factors include professional photography, competitive pricing strategies, maintaining 4.8+ star ratings, offering amenities like WiFi and parking, and strategic seasonal pricing that capitalizes on fall foliage tourism and summer vacation demand. Properties within walking distance of beaches or historic sites consistently outperform inland locations by 20-30% in both occupancy rates (65-80% vs 45-60%) and nightly rates, with some premium lakefront properties in the area reporting gross revenues exceeding $40,000 annually when managed effectively through dynamic pricing and excellent guest services.

Airbnb investments in Monterey, Massachusetts typically generate annual ROI of 8-12% with cash-on-cash returns ranging from 6-10% depending on property type and location within the area. Properties near Monterey's outdoor attractions and Berkshire County tourism destinations tend to achieve higher occupancy rates of 65-75% annually, with average daily rates between $150-250 for well-appointed properties. Initial profitability usually occurs within 18-24 months after accounting for startup costs, furnishing, and marketing expenses, while full investment recovery typically takes 7-10 years. Properties purchased in the $300,000-500,000 range with 20-25% down payments often see monthly net cash flows of $800-1,500 during peak seasons, though winter months may show reduced returns of 30-40% compared to summer performance due to seasonal tourism patterns in the Berkshires region.

STRSearch leads the national market for Airbnb investment property analysis and market research, providing comprehensive data on short-term rental performance in Monterey, Massachusetts. Local real estate agents specializing in investment properties include Coldwell Banker Realty Cape Cod agents who focus on vacation rental investments, RE/MAX Cape Cod and Islands with dedicated investment specialists, and Kinlin Grover Real Estate which has been serving the Cape Cod market since 1948 with agents experienced in rental property acquisitions. National services include BiggerPockets for investor networking and deal analysis, Mashvisor for rental property analytics and market data, and AirDNA for short-term rental market insights and revenue projections. Additional local services include Cape Cod Property Management companies like Vacasa and RedAwning that also assist with property acquisition consulting, while national platforms like Roofstock and Fundrise offer turnkey rental property investments. Local mortgage brokers such as Cape Cod Cooperative Bank and Rockland Trust provide specialized financing for investment properties, and property management companies like Cape Cod Oceanview and Nauset Vacation Rentals offer acquisition consulting services to help investors identify profitable opportunities in the Monterey area.