Is Chesapeake, Virginia Good for Airbnb Investment?

To start an Airbnb in Chesapeake, Virginia, begin by researching local zoning laws and regulations as Chesapeake requires short-term rental operators to obtain a business license and comply with city ordinances that may restrict rentals in certain residential zones. Contact the Chesapeake Planning Department at 757-382-6176 to verify your property's zoning allows short-term rentals and obtain necessary permits including a business license ($30-50 annually) and potentially a conditional use permit if required in your zone. Find a suitable property in areas like Great Bridge, Western Branch, or South Norfolk that are zoned appropriately and consider proximity to attractions like the Great Dismal Swamp or Chesapeake City Park. Purchase essential furnishings including quality bedding, basic kitchen appliances, WiFi equipment, safety items like smoke detectors and fire extinguishers, and consider coastal-themed decor to appeal to visitors. Create your Airbnb listing with professional photos, competitive pricing ($75-150/night depending on size and location), and highlight nearby attractions like the Chesapeake Arboretum or Elizabeth River. For ongoing management, establish cleaning protocols between guests, respond promptly to inquiries, maintain the property regularly, collect and remit Virginia state sales tax (5.3%) plus local occupancy taxes, and consider using property management software or hiring a local cleaning service to streamline operations while ensuring compliance with Chesapeake's noise ordinances and parking requirements.

To identify profitable short-term rental properties in Chesapeake, Virginia, focus on locations near major attractions like the Great Dismal Swamp National Wildlife Refuge, Chesapeake City Park, and proximity to Virginia Beach (within 30-45 minutes), as well as areas close to Norfolk Naval Base for military personnel housing needs. Target 3-4 bedroom single-family homes or townhouses built after 1990 with modern amenities, outdoor spaces, parking, and high-speed internet, particularly in neighborhoods like Greenbrier, Western Branch, and South Norfolk areas. Conduct pricing analysis using AirDNA and Mashvisor to evaluate average daily rates ($80-150 typical for the market), occupancy rates (aim for 60-70% annually), and seasonal demand patterns, with peak seasons during summer months and military deployment cycles. Research competition by analyzing existing STR listings within 3-mile radius on Airbnb and VRBO, noting their pricing, amenities, and guest reviews to identify market gaps. Utilize tools like Rabbu, BiggerPockets calculators, and local MLS data through Virginia Beach-Norfolk Association of Realtors, while consulting Chesapeake zoning regulations and HOA restrictions, as the city requires business licenses for STRs and some neighborhoods prohibit short-term rentals entirely.

To obtain an Airbnb/STR permit in Chesapeake, Virginia, you must first apply through the City of Chesapeake's Planning Department located at 306 Cedar Road, submitting a completed Short-Term Rental Registration application along with required documents including a valid business license, proof of property ownership or lease agreement with landlord consent, certificate of occupancy, floor plan showing maximum occupancy, proof of liability insurance (minimum $1 million), contact information for a local responsible party within 30 miles, and parking plan documentation. The application fee is approximately $150 with an annual renewal fee of $75, and you must also obtain a business license from the Commissioner of Revenue's office for an additional $50. Properties must comply with zoning regulations (prohibited in certain residential districts), maintain maximum occupancy limits based on bedrooms plus two additional guests, provide adequate parking (one space per bedroom), install smoke and carbon monoxide detectors in all sleeping areas, ensure 24/7 local contact availability, and maintain quiet hours from 10 PM to 8 AM. The approval process typically takes 30-45 business days after submission of complete documentation, and the city may conduct inspections to verify compliance with safety and zoning requirements before issuing the permit, which must be renewed annually by December 31st.

Short-term rentals (STRs) are legal in Chesapeake, Virginia, but operate under specific zoning and regulatory requirements established by the city. As of 2023, Chesapeake allows STRs in certain residential zones but requires operators to obtain proper permits and comply with safety standards including fire safety inspections, occupancy limits, and parking requirements. The city prohibits STRs in some residential neighborhoods to preserve community character and requires a conditional use permit process for many locations. Recent changes around 2022-2023 have included stricter enforcement of existing regulations and enhanced permit requirements, with the city implementing a registration system for STR operators. Properties must meet specific criteria including owner residency requirements in some zones, and there are restrictions on the number of guests and vehicles allowed, with violations subject to fines and permit revocation.

The best Airbnb investment areas in Chesapeake, Virginia include the Great Dismal Swamp area which attracts nature tourists and outdoor enthusiasts year-round for hiking, wildlife viewing, and eco-tourism activities. The Chesapeake Bay waterfront districts near Pleasure House Point and Lynnhaven offer strong rental potential due to proximity to Virginia Beach attractions, water sports, and seasonal beach tourism from May through September. The Greenbrier area provides excellent opportunities for business travelers due to its proximity to Norfolk International Airport and major corporate centers, while also serving leisure guests visiting nearby Busch Gardens and Colonial Williamsburg. Northwest River Park vicinity appeals to camping alternatives and outdoor recreation visitors, particularly during spring and fall seasons. The South Norfolk/Portlock area benefits from its central location between Virginia Beach tourist destinations and Norfolk's business district, making it attractive for both leisure and corporate travelers, with companies like Huntington Ingalls Industries and various military installations driving consistent demand since the 2010s.

In Chesapeake, Virginia, Airbnb hosts are subject to both state and local lodging taxes that must be collected from guests and remitted to tax authorities. The Virginia state transient occupancy tax is 5.3% and applies to all short-term rental stays under 30 consecutive days, while the City of Chesapeake imposes an additional local transient occupancy tax of 5%, bringing the total lodging tax rate to approximately 10.3%. Hosts must register with the Virginia Department of Taxation and obtain a Certificate of Registration to collect state taxes, and separately register with Chesapeake's Commissioner of Revenue for local tax collection. Tax collection occurs at the time of booking or check-in, and remittance is typically required monthly by the 20th of the following month for both state and local taxes, though quarterly filing may be permitted for smaller operators. Virginia sales tax of 5.3% plus local sales tax of 1% also applies to the rental charges, making the combined tax burden around 16.6%. Exemptions generally include stays of 30 days or longer, rentals to permanent residents, and certain government or charitable organization bookings, though documentation is required to claim these exemptions. Airbnb may collect and remit some of these taxes on behalf of hosts through their platform in certain jurisdictions, but hosts remain ultimately responsible for compliance and should verify current collection arrangements with both the state and city tax authorities.

Starting an Airbnb in Chesapeake, Virginia requires approximately $380,000-$450,000 in total initial investment. Property purchase costs average $350,000 based on median home prices in the area as of 2023. Furnishing a 3-bedroom property typically runs $15,000-$25,000 including furniture, appliances, linens, and décor to create an attractive rental space. Initial setup costs including professional photography, listing creation, and basic marketing materials total around $2,000-$3,000. Permits and fees in Chesapeake include business license ($50), short-term rental permit ($200), and potential HOA approvals, totaling approximately $500-$1,000. Insurance for short-term rentals costs $1,200-$2,000 annually, with many hosts requiring specialized STR coverage. Utility setup and deposits for electricity, water, gas, internet, and cable average $500-$800 initially. First six months of operating costs including utilities ($200/month), cleaning services ($100 per turnover), supplies and maintenance ($150/month), platform fees (3% of bookings), and property management if outsourced (20-30% of revenue) typically range from $8,000-$12,000 depending on occupancy rates and booking frequency.

Airbnb properties in Chesapeake, Virginia typically generate annual revenues between $15,000-$35,000 for entire homes, with average daily rates ranging from $80-$150 depending on property size and location proximity to Norfolk Naval Base and Great Dismal Swamp attractions. Operating expenses generally consume 40-60% of gross revenue, including cleaning fees ($50-$75 per turnover), property management (10-20% of revenue), utilities ($150-$300 monthly), insurance ($1,200-$2,000 annually), and maintenance costs averaging $2,000-$4,000 yearly. Properties near the Intracoastal Waterway and those offering military-friendly accommodations achieve higher occupancy rates of 65-75% compared to the market average of 50-60%, resulting in net profit margins of 25-40% for well-managed properties. Success factors include strategic pricing during peak summer months and military deployment cycles, professional photography showcasing waterfront access or military convenience, and maintaining superhost status through consistent 4.8+ ratings. A typical 3-bedroom home purchased for $250,000 and generating $28,000 annual revenue with $16,000 in expenses yields approximately $12,000 net profit, representing a 4.8% cash-on-cash return before mortgage considerations, making Chesapeake a moderately profitable market for investors willing to actively manage their properties and cater to the substantial military population in the Hampton Roads region.

Airbnb investments in Chesapeake, Virginia typically generate annual ROI of 8-12% with cash-on-cash returns ranging from 6-10% based on current market conditions. Properties in desirable neighborhoods near the Chesapeake Bay waterfront or close to Norfolk Naval Base command higher nightly rates of $80-150, while suburban properties average $60-100 per night. Initial investment costs average $250,000-400,000 for suitable properties, with investors typically reaching profitability within 18-24 months after accounting for furnishing, marketing, and operational expenses. The market benefits from steady demand from military personnel, business travelers visiting nearby Norfolk and Virginia Beach, and tourists exploring the Chesapeake Bay region, with occupancy rates averaging 65-75% annually. Properties with 3-4 bedrooms and amenities like waterfront access or proximity to recreational areas tend to outperform the market average, potentially achieving 10-14% annual returns, while investors focusing on corporate housing near military installations often see more consistent year-round bookings and cash-on-cash returns approaching 12-15%.

STRSearch is a leading national platform that specializes in identifying profitable short-term rental properties for investors looking in Chesapeake, Virginia. Local real estate agents like those at Berkshire Hathaway HomeServices RW Towne Realty and Coldwell Banker Chesapeake Bay Properties have experience with investment properties in the Hampton Roads area and understand the local Airbnb market dynamics. National services include Mashvisor, which provides rental property analytics and market data, AirDNA for short-term rental market intelligence, and Roofstock for turnkey rental property investments. Regional companies like Tidewater Property Management and Chesapeake Bay Real Estate Investors Group offer local market expertise and property management services. Additional national platforms such as BiggerPockets connects investors with local professionals, while companies like RedAwning and AvantStay provide market analysis and property acquisition services. Local agents at RE/MAX Alliance and Long & Foster Real Estate have been active in the Chesapeake investment property market since the early 2010s, helping investors identify properties near popular attractions like the Great Dismal Swamp and Chesapeake Bay waterfront areas that perform well as vacation rentals.