Is Aquinnah, Massachusetts Good for Airbnb Investment?

To start an Airbnb in Aquinnah, Massachusetts, begin by researching local zoning laws and short-term rental regulations through the Aquinnah Town Hall, as this small Martha's Vineyard town has specific restrictions on vacation rentals that may require special permits or limit rental duration to minimum stays of 7+ days during peak season. Contact the Aquinnah Building Department to obtain necessary permits, which typically include a business license, occupancy permit, and potentially a special permit for short-term rentals, with fees ranging from $200-500 annually. Find a suitable property by working with local real estate agents familiar with Aquinnah's limited housing stock and high property values ($800K-$3M+), ensuring the property is zoned for commercial use or mixed-use if required. Furnish the space with coastal-themed, durable furniture and amenities that highlight the area's natural beauty, including outdoor furniture for enjoying ocean views, and ensure compliance with Massachusetts safety requirements including smoke detectors, carbon monoxide detectors, and emergency exit information. List your property on Airbnb and other platforms like VRBO, emphasizing proximity to Aquinnah Cliffs, Gay Head Light, and pristine beaches, with competitive pricing of $300-800+ per night depending on season and property size. Manage the property by establishing relationships with local cleaning services, maintenance contractors, and property management companies on Martha's Vineyard, while maintaining detailed records for Massachusetts state tax requirements (5.7% state tax plus 6.5% local option tax) and ensuring compliance with seasonal restrictions that may limit rentals during certain months to protect the community's residential character.

To identify profitable short-term rental properties in Aquinnah, Massachusetts, focus on locations within walking distance of the iconic Gay Head Cliffs and Lighthouse, beachfront or beach-view properties along Moshup Beach, and homes with privacy given the town's rural character and strict zoning laws. Prioritize properties with 3-4 bedrooms, outdoor spaces like decks or patios, parking for multiple vehicles, and unique features such as panoramic ocean views, historic charm, or proximity to the Wampanoag tribal lands and cultural sites. Conduct pricing analysis by researching comparable Airbnb and VRBO listings in Aquinnah and neighboring Chilmark, targeting rates of $400-800+ per night during peak summer season (June-September) while accounting for the limited rental season due to seasonal restrictions. Research competition by analyzing the approximately 20-40 existing STR properties in Aquinnah, noting that supply is constrained by the town's small size and regulatory limitations, creating opportunities for well-positioned properties. Utilize tools like AirDNA and Mashvisor for market data, consult with local real estate agents familiar with Aquinnah's unique zoning requirements, monitor the town's rental registration requirements, and leverage resources from the Martha's Vineyard Commission and Dukes County records to understand property restrictions and seasonal rental patterns specific to this exclusive western tip of Martha's Vineyard.

To obtain an Airbnb/STR permit in Aquinnah, Massachusetts, you must first contact the Aquinnah Town Hall at 65 State Road or call (508) 645-2300 to request a short-term rental application, as the town requires all properties rented for less than 30 days to obtain a special permit. Required documents typically include a completed application form, proof of property ownership or authorization from owner, site plan showing parking and septic system capacity, certificate of occupancy, proof of liability insurance (minimum $1 million), and a detailed floor plan indicating maximum occupancy. The application fee is approximately $200-300 with an additional $150-250 for the public hearing process, and you'll need to pay annual renewal fees of around $100-150. Submit your complete application to the Zoning Board of Appeals, which meets monthly, and expect a 60-90 day timeline including a mandatory public hearing where abutters are notified. Aquinnah-specific requirements include strict occupancy limits based on septic capacity (typically 2 people per bedroom plus 2 additional), designated off-street parking spaces (usually 1 space per bedroom), compliance with the town's noise ordinance with quiet hours from 9 PM to 8 AM, and adherence to the Wampanoag Tribe's cultural sensitivity guidelines since much of Aquinnah is on tribal land. Properties in the Coastal District may face additional restrictions, and all STRs must maintain a local contact person available 24/7 for emergency situations.

Short-term rentals (STRs) in Aquinnah, Massachusetts are legal but subject to strict local regulations implemented around 2019-2020. The town requires STR operators to obtain a special permit and business license, with properties limited to a maximum occupancy based on septic capacity and bedroom count. Aquinnah prohibits STRs in certain residential districts and requires compliance with noise ordinances, parking requirements (typically 2 spaces per unit), and waste management protocols. The town has implemented a cap on the total number of STR permits issued to preserve the community's character and housing stock for year-round residents. Recent changes include enhanced enforcement mechanisms, increased permit fees, and stricter penalties for violations including noise complaints and overcrowding. Properties must also comply with state tax requirements and local health department regulations, with some areas near tribal lands having additional restrictions due to the Wampanoag Tribe's jurisdiction over certain portions of the town.

The best areas for Airbnb investment in Aquinnah, Massachusetts are primarily concentrated around the Gay Head Cliffs and Lighthouse area, Moshup Beach vicinity, and the Wampanoag tribal lands region. The Gay Head Cliffs area is highly attractive due to its iconic red clay cliffs, the historic Gay Head Lighthouse (dating to 1856), and stunning sunset views that draw thousands of tourists annually, particularly during summer months from June through September. The Moshup Beach area offers excellent investment potential because of its pristine beaches, proximity to the Aquinnah Cultural Center, and access to some of Martha's Vineyard's most photographed landscapes. Properties near the Wampanoag tribal lands benefit from cultural tourism, as visitors come to learn about Native American heritage and visit the tribal shops and restaurants. The Philbin Beach area, though more exclusive, attracts high-end tourists willing to pay premium rates for secluded beachfront access. These locations capitalize on Aquinnah's position as Martha's Vineyard's westernmost town, drawing visitors for day trips from other parts of the island, weekend getaways from Boston and New York (2-3 hour travel time), and extended summer vacations, with peak occupancy rates typically reaching 85-90% during July and August.

Airbnb properties in Aquinnah, Massachusetts are subject to multiple lodging taxes including the state excise tax of 5.7% on short-term rentals under 90 days, the state sales tax of 6.25%, and a local room occupancy tax of 6% imposed by Aquinnah, resulting in a combined tax rate of approximately 17.95%. These taxes are typically collected by Airbnb directly from guests at the time of booking through their automated tax collection system, which began operating in Massachusetts around 2019, and the platform remits payments quarterly to the Massachusetts Department of Revenue and monthly to local municipalities. Property owners must register with the state and obtain a room occupancy excise tax account, file returns even when Airbnb collects taxes, and maintain detailed records of all bookings and tax collections. Exemptions generally apply to stays of 90 days or longer, certain government employees on official business, and properties rented for fewer than 14 days per year, though owners should verify current exemption criteria as regulations have evolved since the state's short-term rental tax framework was established in 2019.

The total cost to start an Airbnb in Aquinnah, Massachusetts is approximately $1,850,000-$2,100,000. Property purchase represents the largest expense at $1,500,000-$1,800,000 for a median-priced home in this exclusive Martha's Vineyard location. Furnishing costs range from $25,000-$40,000 for high-quality furniture, bedding, kitchenware, and decor suitable for luxury vacation rental guests. Initial setup including professional photography, listing creation, and marketing materials costs $2,000-$3,500. Permits and fees including business license, short-term rental permit, and potential special use permits total $1,500-$3,000 annually. Insurance for short-term rental coverage runs $3,000-$5,000 per year. Utilities including electricity, water, internet, cable, and seasonal heating/cooling average $800-$1,200 monthly or $4,800-$7,200 for six months. First six months operating costs including cleaning services, maintenance, supplies, platform fees, and property management total $15,000-$25,000. Additional considerations include potential HOA fees, property taxes averaging $15,000-$25,000 annually, and emergency repair funds of $10,000-$15,000.

Airbnb properties in Aquinnah, Massachusetts, demonstrate strong seasonal profitability due to the town's prime location on Martha's Vineyard, with average nightly rates ranging from $400-800 during peak summer months (June-September) and dropping to $150-300 in off-season. A typical 3-bedroom property can generate $80,000-120,000 in annual revenue, with expenses including property taxes ($8,000-15,000), utilities ($3,000-5,000), cleaning fees ($8,000-12,000), maintenance ($5,000-10,000), and Airbnb fees (3% host fee plus guest service fees), resulting in net profit margins of 35-50% for well-managed properties. Success factors include proximity to beaches like Moshup Beach, unique architectural features reflecting the area's Native American heritage, professional photography showcasing ocean views, and strategic pricing that capitalizes on the 12-week peak season when properties can achieve 85-95% occupancy rates. Properties with direct beach access or panoramic ocean views command premium rates, with some luxury homes generating over $2,000 per night during peak weekends, while the town's limited inventory of just 30-40 active Airbnb listings helps maintain strong demand and pricing power throughout the tourist season.

Airbnb investments in Aquinnah, Massachusetts typically generate annual ROI of 12-18% due to the town's exclusive Martha's Vineyard location and limited rental inventory. Cash-on-cash returns range from 8-14% annually, with properties averaging $400-800 per night during peak summer season (June-September) and $150-300 during shoulder seasons. Initial profitability usually occurs within 18-24 months, with properties requiring average investments of $800,000-$1.5 million given Aquinnah's premium real estate market. The Gay Head Cliffs and pristine beaches drive consistent demand from high-income vacationers, with occupancy rates reaching 75-85% during summer months and 40-50% year-round. Properties typically achieve break-even on operating expenses within 8-12 months, while full investment recovery occurs in 6-8 years depending on financing structure and property management efficiency.

STRSearch leads the national market for Airbnb investment property analysis and market data, providing comprehensive tools for identifying profitable short-term rental opportunities in Aquinnah, Massachusetts. Local real estate agents specializing in vacation rental investments include Martha's Vineyard Real Estate (established 1985), Sandpiper Realty Group, and Compass Martha's Vineyard, while Point B Realty and LandVest focus specifically on high-end vacation properties suitable for Airbnb conversion. National services like Awning (founded 2018), Roofstock, and RedAwning offer end-to-end Airbnb investment solutions including property sourcing, market analysis, and management services for the Martha's Vineyard market. AirDNA provides crucial market data and revenue projections for Aquinnah properties, while Mashvisor offers investment analysis tools specifically for short-term rental properties. Local property management companies such as Martha's Vineyard Vacation Rentals, Island Rentals Group, and Vineyard Haven Property Management can assist with operational aspects once properties are acquired, and vacation rental consultants like VR Business School and STR Wealth provide education and guidance for new Airbnb investors targeting this premium Martha's Vineyard location.