Is Dennis, Massachusetts Good for Airbnb Investment?

To start an Airbnb in Dennis, Massachusetts, begin by researching local zoning laws and short-term rental regulations through the Dennis Town Hall, as Cape Cod municipalities have varying restrictions on vacation rentals, with some requiring special permits or limiting rental duration to minimum 7-day stays during peak season. Obtain necessary permits including a business certificate from the Town Clerk, register for Massachusetts state taxes, and secure appropriate insurance coverage that includes short-term rental liability. Find a suitable property by purchasing or leasing in areas zoned for residential or mixed-use, ensuring compliance with Dennis's density requirements and parking regulations, with properties near Dennis beaches, Cape Cod Rail Trail, or Scargo Lake commanding premium rates of $150-400 per night seasonally. Furnish the space with coastal-themed decor, essential amenities including linens, kitchen supplies, WiFi, and outdoor furniture for decks or patios, budgeting $8,000-15,000 for a complete setup. Create your Airbnb listing with professional photography highlighting proximity to Dennis beaches like Mayflower Beach or Corporation Beach, Cape Cod attractions, and seasonal activities, setting competitive rates that reflect the $200-350 average nightly rate for Dennis properties during summer months. Manage the property by establishing cleaning protocols between guests, coordinating key exchanges or installing smart locks, responding promptly to guest communications, and maintaining the property year-round while navigating Dennis's seasonal rental market that peaks from May through September with significantly lower winter demand.

To identify profitable short-term rental properties in Dennis, Massachusetts, focus on locations within 0.5-1 mile of popular beaches like Mayflower Beach, Corporation Beach, and Chapin Beach, as well as properties near Dennis Port's commercial district and Route 28 corridor. Target 3-4 bedroom single-family homes or condos with 2+ bathrooms, outdoor spaces like decks or patios, parking for 2+ cars, and amenities such as air conditioning, WiFi, and beach equipment storage, as these features command premium rates of $200-400 per night during peak summer season (June-August). Conduct pricing analysis using AirDNA and Mashvisor to evaluate average daily rates, occupancy rates (typically 60-75% in Dennis), and seasonal demand patterns, while researching competition through Airbnb and VRBO searches within 2-mile radius to identify market saturation and pricing gaps. Utilize tools like STR Helper for permit research, as Dennis requires special permits for short-term rentals, and leverage local resources including the Dennis Chamber of Commerce, Cape Cod MLS data, and vacation rental management companies like Cape Cod Oceanview and Vacasa for market insights. Properties priced between $400,000-$800,000 with strong rental histories typically generate 8-12% annual returns when managed effectively, with waterfront or water-view properties commanding the highest premiums in this seasonal Cape Cod market.

To obtain an Airbnb/STR permit in Dennis, Massachusetts, you must first register with the Massachusetts Department of Revenue for state lodging taxes and obtain a Certificate of Registration, then apply directly to the Town of Dennis Building Department or Planning Department for a short-term rental permit. Required documents typically include a completed application form, proof of property ownership or lease agreement, floor plan of the rental unit, certificate of occupancy, proof of liability insurance (minimum $1 million), contact information for a local representative available 24/7, and payment of applicable fees. The town permit fee is estimated at $200-400 annually, plus state registration fees of approximately $200, and you may need additional inspections costing $100-200. The timeline is generally 4-8 weeks from submission of a complete application, though initial applications may take longer due to required inspections by the fire department and building inspector. Dennis-specific requirements include maintaining the property as your primary residence if operating a homestay, limiting occupancy to no more than 2 guests per bedroom with a maximum of 8-10 guests total, providing adequate parking spaces, ensuring compliance with septic system capacity, maintaining quiet hours typically from 9 PM to 8 AM, and having a local contact person available within 30 minutes response time who can address any issues that arise during guest stays.

Short-term rentals (STRs) are legal in Dennis, Massachusetts, but subject to local regulations and state oversight. The town of Dennis allows STRs through a licensing system that requires property owners to obtain permits, comply with health and safety standards, and adhere to occupancy limits typically based on septic capacity and bedroom count. Properties must meet specific requirements including smoke and carbon monoxide detectors, emergency contact information, and parking provisions. Dennis has implemented restrictions on the number of guests, quiet hours (usually 10 PM to 8 AM), and requires hosts to maintain liability insurance. The town prohibits STRs in certain residential zones or may limit them to specific districts, and there are often restrictions on properties within 150 feet of conservation areas or wetlands. Recent changes around 2018-2021 included stricter enforcement mechanisms, higher penalties for violations, and enhanced registration requirements following statewide legislation that gave municipalities greater authority to regulate STRs while requiring them to collect state taxes through platforms like Airbnb and VRBO.

The best areas for Airbnb investment in Dennis, Massachusetts are Dennis Port, West Dennis Beach area, and Scargo Lake vicinity. Dennis Port offers prime beachfront access to Nantucket Sound with numerous vacation rentals commanding premium rates during summer months, attracting families and beach enthusiasts from Boston and New York metropolitan areas. The West Dennis Beach district provides excellent rental potential due to its proximity to one of Cape Cod's most popular beaches, the Cape Cod Rail Trail, and numerous restaurants and shops along Route 28, making it ideal for tourists seeking both beach access and entertainment options. The Scargo Lake area appeals to visitors wanting a quieter, more secluded Cape Cod experience while still being close to Dennis's cultural attractions like the Cape Playhouse and Dennis Historical Society museums, plus it offers year-round appeal for guests interested in hiking, fishing, and fall foliage viewing. These locations benefit from Dennis's position as a mid-Cape destination that's easily accessible from major highways while offering authentic Cape Cod charm, strong summer tourism from Memorial Day through Labor Day, and growing shoulder season demand from visitors seeking off-peak Cape Cod experiences.

In Dennis, Massachusetts, Airbnb hosts are subject to multiple lodging taxes including the state excise tax of 5.7% on short-term rentals under 90 days, Barnstable County's 2.75% county excise tax, and Dennis's local room occupancy tax of 6%, totaling approximately 14.45% in combined taxes. The Massachusetts Department of Revenue requires hosts to register for a tax account and collect these taxes from guests at the time of booking or check-in, with monthly remittance due by the 20th of the following month for state and county taxes, while local taxes are typically remitted quarterly to the Town of Dennis. Airbnb can collect and remit these taxes automatically for hosts who opt into their tax collection service, though hosts remain ultimately responsible for compliance. Exemptions may apply for stays exceeding 90 consecutive days, certain medical or emergency accommodations, and rentals to permanent residents, though documentation is required. Hosts must maintain detailed records of all bookings, tax collections, and payments, and failure to comply can result in penalties, interest charges, and potential legal action by tax authorities.

To start an Airbnb in Dennis, Massachusetts, expect total costs around $485,000-$520,000. Property purchase represents the largest expense at approximately $400,000-$425,000 based on median home prices in Dennis as of 2023. Furnishing costs typically range $15,000-$25,000 for a complete 2-3 bedroom property 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 in Dennis include short-term rental registration ($200-$500), business license ($50-$100), and potential zoning compliance costs ($500-$1,500). Insurance premiums for short-term rental coverage run $2,000-$3,500 annually, with first year paid upfront. Utility deposits and connections for electricity, gas, water, internet, and cable total approximately $1,000-$2,000. First six months operating costs encompass utilities ($1,800), cleaning services ($2,400), maintenance reserves ($1,500), Airbnb platform fees ($3,000), marketing ($500), and miscellaneous supplies ($800), totaling roughly $10,000. Additional considerations include potential HOA fees, property taxes, and emergency repair funds which could add another $5,000-$10,000 to initial capital requirements.

Airbnb properties in Dennis, Massachusetts, located on Cape Cod, typically generate annual revenues between $25,000-$45,000 for seasonal properties and $35,000-$65,000 for year-round rentals, with peak summer months (June-August) commanding nightly rates of $200-$400 compared to off-season rates of $80-$150. Operating expenses generally range from 40-60% of gross revenue, including property management fees (15-25%), cleaning costs ($75-$125 per turnover), utilities ($2,000-$4,000 annually), insurance ($1,500-$3,000), maintenance ($3,000-$6,000), and Cape Cod's relatively high property taxes averaging $8,000-$15,000 annually. Properties within walking distance of beaches like Mayflower Beach or Corporation Beach achieve 15-25% higher occupancy rates and premium pricing, while inland properties rely more heavily on competitive pricing and unique amenities. Success factors include professional photography showcasing Cape Cod charm, responsive guest communication, partnerships with local cleaning services, and strategic pricing that captures summer tourism while maintaining winter bookings from visitors to nearby Patriot Place or Boston day-trippers. Net profit margins typically range from 15-35% for well-managed properties, with beachfront cottages and renovated homes featuring modern amenities achieving the higher end of profitability, while properties requiring significant maintenance or lacking distinctive features often struggle to exceed 20% margins in this competitive seasonal market.

Airbnb investments in Dennis, Massachusetts typically generate annual ROI of 8-12% with cash-on-cash returns ranging from 6-10% for properties purchased in the $400,000-$600,000 range. The Dennis market, particularly areas near Cape Cod beaches and Dennis Port, shows strong seasonal demand from May through September with average daily rates of $200-$350 during peak summer months and $120-$180 during shoulder seasons. Properties generally reach profitability within 18-24 months when factoring in initial renovation costs of $15,000-$30,000 for short-term rental preparation, with gross rental yields averaging 10-14% annually. The market benefits from consistent tourism demand, proximity to beaches, and limited hotel inventory, though investors should expect 3-4 month low seasons with significantly reduced bookings, making the typical breakeven timeline 20-30 months for leveraged purchases with 20-25% down payments.

STRSearch is a leading national platform that specializes in identifying profitable short-term rental investment properties across markets including Dennis, Massachusetts. In the Cape Cod area, local real estate agents like Cape Cod & Islands Association of Realtors members including Kinlin Grover Real Estate, Robert Paul Properties, and Coldwell Banker Realty have extensive experience with vacation rental investments in Dennis and surrounding towns. National services such as Mashvisor, BiggerPockets, and AirDNA provide market analysis and property identification tools for Airbnb investors targeting the Cape Cod market. Local property management companies like Cape Cod Oceanview Realty, Vacation Cape Cod, and RedAwning offer turnkey services for investors looking to purchase and operate short-term rentals in Dennis. Additionally, platforms like Roofstock and Awning (now part of RedAwning) have historically offered curated Airbnb-ready investment properties in Massachusetts markets, while local investment groups and real estate professionals specializing in vacation rentals can be found through the Cape Cod Real Estate Investment Association and similar networking organizations that focus on the lucrative summer rental market in Dennis and the broader Cape Cod region.