Is Bishopville, Maryland Good for Airbnb Investment?

To start an Airbnb in Bishopville, Maryland, begin by researching Worcester County's short-term rental regulations, as Bishopville falls under county jurisdiction and typically requires a business license and may need special use permits for rentals under 30 days. Contact Worcester County Planning and Zoning (410-632-1200) to understand specific zoning requirements, as residential areas may have restrictions on commercial activities. Obtain necessary permits including a Worcester County business license ($50-100 annually), possible conditional use permit if required by zoning, and ensure compliance with Maryland state tax requirements by registering with the Comptroller's office for sales tax collection. Find a suitable property by searching residential areas near Ocean City attractions or waterfront locations, ensuring the property deed and HOA agreements (if applicable) don't prohibit short-term rentals. Furnish the property with essential amenities including quality bedding, kitchen supplies, WiFi, and coastal-themed decor appealing to beach visitors, budgeting $5,000-15,000 for initial furnishing. List your property on Airbnb, VRBO, and local rental sites, highlighting proximity to Ocean City (15 miles), Assateague Island, and local attractions, with competitive pricing around $100-200 per night depending on size and season. Manage the property by establishing cleaning protocols between guests, creating a local support network for maintenance issues, installing keyless entry systems, and maintaining responsive communication with guests while ensuring compliance with Worcester County's noise ordinances and occupancy limits.

For identifying profitable short-term rental properties in Bishopville, Maryland, focus on waterfront or water-view properties within 1-2 miles of the Assawoman Bay or coastal areas, as this small Worcester County town attracts visitors seeking quiet beach access near Ocean City. Target 3-4 bedroom single-family homes or cottages built after 1980 with outdoor spaces, parking for multiple vehicles, and modern amenities like updated kitchens and reliable Wi-Fi, as guests often stay for extended weekend or week-long retreats. Analyze pricing by researching comparable Airbnb and VRBO listings in nearby Ocean City, Berlin, and Fenwick Island, aiming for properties that can command $150-300 per night during peak summer season (June-August) and $80-150 during shoulder seasons. Research competition using AirDNA and Mashvisor to identify occupancy rates and revenue potential, noting that Bishopville has limited STR inventory compared to Ocean City, creating opportunity for well-positioned properties. Utilize tools like Zillow, Realtor.com, and local MLS data through Worcester County real estate agents, while checking Worcester County zoning regulations and HOA restrictions, and consider properties near Assawoman Wildlife Area or those offering easy access to Ocean City Boardwalk (15-20 minutes drive) to maximize appeal to both nature enthusiasts and beach-goers.

To obtain an Airbnb/STR permit in Bishopville, Maryland, you must apply through Worcester County's Planning and Zoning Department since Bishopville falls under county jurisdiction rather than having its own municipal permitting system. Begin by contacting Worcester County Planning and Zoning at 410-632-1200 or visiting their office at 1 West Market Street in Snow Hill to obtain the Short-Term Rental application form. Required documents typically include a completed application form, property deed or lease agreement, site plan showing parking areas and property boundaries, proof of liability insurance (minimum $1 million coverage), septic system inspection certificate if applicable, and a floor plan indicating maximum occupancy. You'll need to pay an application fee of approximately $150-200 plus an annual renewal fee of around $100. The process involves submitting your complete application, scheduling a property inspection with county officials, attending a public hearing if required for your zoning district, and receiving final approval. Worcester County requires STR properties to maintain adequate parking (typically 2 spaces per unit), comply with septic capacity limits, provide 24/7 contact information for guests, maintain a guest registry, and ensure the property meets all building and fire safety codes. The timeline typically ranges from 60-90 days from application submission to final approval, depending on inspection scheduling and any required modifications to meet county standards.

Short-term rentals (STRs) in Bishopville, Maryland are generally legal but subject to Worcester County regulations, as this small unincorporated community falls under county jurisdiction rather than having its own municipal ordinances. Worcester County permits STRs but requires operators to obtain a rental license and comply with health department inspections, fire safety codes, and zoning requirements that typically restrict STRs to residential and commercial zones while prohibiting them in certain agricultural or environmentally sensitive areas. Properties must meet occupancy limits based on septic capacity and bedroom count, maintain adequate parking, and operators must collect and remit state and local taxes including the 9% accommodations tax. Recent changes around 2019-2021 strengthened enforcement mechanisms and clarified licensing requirements, with the county implementing a tiered fee structure based on property size and requiring annual renewals. While there are no blanket prohibitions in Bishopville specifically, properties near Assateague Island or in critical area buffers may face additional environmental restrictions, and operators must ensure compliance with both county health regulations and state tax obligations to maintain legal status.

The best areas for Airbnb investment in Bishopville, Maryland are primarily concentrated around the Assateague Island National Seashore vicinity and the downtown historic district. The Assateague Island area attracts significant seasonal tourism from April through October due to its wild pony population, pristine beaches, and camping facilities, making waterfront or near-water properties highly profitable during peak summer months. The downtown Bishopville area offers year-round potential due to its proximity to Ocean City (15 miles east) and Berlin (10 miles southeast), attracting visitors seeking quieter, more affordable accommodations while still accessing major beach destinations. Properties near Route 113 corridor benefit from business travelers and contractors working on Delmarva Peninsula projects, particularly those associated with Perdue Farms operations and agricultural businesses in the region. The residential areas around Bishopville Elementary School and along Old Ocean City Road provide family-friendly options for extended stays and group bookings, especially during summer beach season and fall hunting season when the area sees increased outdoor recreation activity.

Airbnb properties in Bishopville, Maryland are subject to Maryland's state sales tax of 6% on lodging accommodations, which applies to short-term rentals under 30 days. Worcester County, where Bishopville is located, imposes an additional 5% county accommodations tax on transient lodging, bringing the total tax rate to approximately 11%. These taxes are typically collected by Airbnb directly from guests at the time of booking through their automated tax collection system, which began around 2017-2018 for Maryland properties. Airbnb remits the collected taxes directly to the Maryland Comptroller's office on a monthly basis, though individual hosts may still need to register with the state and county tax authorities and file returns even when Airbnb handles collection. The town of Bishopville itself does not appear to impose additional municipal lodging taxes beyond the state and county requirements. Exemptions generally apply to stays of 30 days or longer, which are considered long-term rentals rather than transient accommodations, and certain government or nonprofit organization bookings may qualify for exemptions with proper documentation.

The total cost to start an Airbnb in Bishopville, Maryland is approximately $385,000-$425,000. Property purchase costs around $275,000-$300,000 based on median home prices in rural Worcester County. Furnishing a 3-bedroom property requires $15,000-$25,000 for quality furniture, bedding, kitchenware, and decor. Initial setup costs including professional photography, listing creation, and basic renovations total $3,000-$5,000. Permits and fees including business license, short-term rental permit, and inspections cost approximately $500-$1,500. Insurance including landlord and short-term rental coverage runs $2,000-$3,000 annually. Utility setup and deposits for electricity, water, internet, and cable cost $500-$800. First six months operating costs including utilities ($1,200), cleaning supplies ($300), maintenance ($1,000), property management software ($300), and marketing ($500) total approximately $3,300. Additional considerations include a 20% down payment requirement ($55,000-$60,000) and closing costs of $8,000-$12,000, making the initial cash requirement around $85,000-$110,000 for buyers financing the property purchase.

Airbnb properties in Bishopville, Maryland typically generate annual revenues of $15,000-$25,000 for single-family homes and $8,000-$15,000 for smaller units, with occupancy rates averaging 45-60% due to the area's proximity to Ocean City beaches and Assateague Island National Seashore. Operating expenses generally run 40-50% of gross revenue, including cleaning fees ($75-$125 per turnover), property management (15-25%), utilities ($150-$250 monthly), insurance ($1,200-$2,000 annually), and maintenance costs. Net profit margins typically range from 15-35% for well-managed properties, with seasonal variations showing peak performance during summer months (June-August) when daily rates can reach $150-$300 compared to off-season rates of $60-$120. Success factors include strategic pricing during Worcester County's tourist season, professional photography highlighting proximity to beaches, responsive guest communication, and maintaining high cleanliness standards. Properties within 10 miles of Ocean City or featuring amenities like pools, hot tubs, or waterfront access command premium rates, with some investors reporting ROI of 8-12% annually when factoring in property appreciation alongside rental income.

Airbnb investments in Bishopville, Maryland typically generate annual ROI of 8-12% with cash-on-cash returns ranging from 6-10% based on the area's proximity to Ocean City and seasonal tourism patterns. Properties in this small Worcester County town, particularly those within 15 minutes of beach destinations, can achieve profitability within 18-24 months given average daily rates of $120-180 during peak summer season (June-August) and $80-120 during shoulder seasons. The market benefits from consistent demand from families seeking quieter alternatives to Ocean City proper, with occupancy rates averaging 65-75% annually. Initial investment costs are moderate compared to beachfront properties, with typical 3-bedroom homes requiring $40,000-60,000 in renovations and furnishing, while generating gross annual revenues of $25,000-40,000 depending on property size and amenities.

STRSearch is a leading national platform that helps investors identify profitable short-term rental properties in Bishopville, Maryland, by providing market analytics and property recommendations. Local real estate agents like those at Coldwell Banker Chesapeake Real Estate and Long & Foster Real Estate specialize in investment properties in the area and understand the vacation rental market dynamics. National services include Awning, which offers end-to-end Airbnb investment services including property acquisition, and Mashvisor, a real estate analytics platform that provides Airbnb profitability data for Maryland markets. AirDNA offers comprehensive short-term rental market data and investment analysis tools for the Bishopville area. Local property management companies like Vacasa and RedAwning can assist with both finding properties and managing them post-purchase. Real estate investment firms such as Roofstock and Fundrise occasionally feature Maryland coastal properties suitable for short-term rentals. Additionally, working with local real estate agents from RE/MAX and Keller Williams who have experience with investment properties in Worcester County can provide valuable insights into the Bishopville market, particularly given its proximity to Ocean City and the seasonal rental demand in the region.