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 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 Greenbrier, Western Branch, or Great Bridge that are zoned for commercial or mixed-use activities, or ensure residential properties comply with HOA restrictions and city setback requirements. Furnish the space with quality furniture, linens, kitchen essentials, and safety equipment including smoke detectors, carbon monoxide detectors, and fire extinguishers as required by Virginia fire codes. Create your Airbnb listing with professional photos, competitive pricing ($75-150/night depending on location and amenities), and detailed descriptions highlighting proximity to Norfolk Botanical Garden, Chesapeake City Park, or Great Dismal Swamp. Manage your property by establishing check-in procedures, maintaining cleanliness standards, responding promptly to guests, collecting Virginia state sales tax (5.3%) plus local occupancy taxes, and ensuring compliance with ongoing city inspections and neighbor relations to maintain your operating permits.

To identify profitable short-term rental properties in Chesapeake, Virginia, focus on locations near the Great Dismal Swamp National Wildlife Refuge, Chesapeake City Park, and areas within 20-30 minutes of Virginia Beach and Norfolk for tourist spillover demand. Target 3-4 bedroom single-family homes or townhouses built after 1990 with modern amenities, outdoor spaces, parking, and proximity to major highways like I-64 and I-464 for easy access to military bases and attractions. Analyze pricing using AirDNA and Mashvisor to benchmark against comparable properties, aiming for average daily rates of $80-150 depending on size and location, with occupancy rates of 60-75% being realistic for the market. Research competition by examining existing Airbnb and VRBO listings within 3-mile radius, identifying gaps in amenities or underserved areas, particularly focusing on properties that cater to military families given the proximity to Naval Station Norfolk and Joint Base Langley-Eustis. Utilize tools like Rabbu, STR Helper, and local MLS data through Virginia Beach-Norfolk Association of Realtors, while monitoring seasonal demand patterns that peak during summer months and military PCS seasons, and ensure compliance with Chesapeake's zoning regulations which generally allow STRs in residential areas with proper permits.

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 Special Use Permit application since short-term rentals require special approval in residential zones. Required documents include a completed SUP application form, site plan showing the property layout, proof of property ownership or lease agreement, floor plan of the rental unit, parking plan demonstrating adequate off-street parking, and a detailed operational plan describing how the rental will be managed. The application fee is approximately $1,200 for the Special Use Permit plus additional fees for public notices and administrative processing, totaling around $1,500-$2,000. The timeline typically takes 3-4 months as the application must go through staff review, Planning Commission review, and City Council approval, with required public hearings at both the Planning Commission and City Council levels. Specific Chesapeake requirements include maintaining the property's residential character, providing one parking space per bedroom plus one additional space, ensuring compliance with all building and fire codes, obtaining a business license, collecting and remitting local taxes, maintaining liability insurance, and adhering to occupancy limits based on the number of bedrooms and square footage of the dwelling unit.

Short-term rentals (STRs) are legal in Chesapeake, Virginia, but operate under specific regulations established by the city. As of 2023, Chesapeake requires STR operators to obtain a business license and comply with zoning requirements, with rentals generally permitted in residential areas but subject to occupancy limits and safety standards including smoke detectors and fire extinguishers. The city prohibits STRs in certain residential zones and requires operators to maintain liability insurance, provide emergency contact information, and ensure properties meet health and safety codes. Recent changes include stricter enforcement of noise ordinances and parking requirements, with violations potentially resulting in license revocation. Properties must also comply with Virginia's statewide STR tax collection requirements, and operators are subject to regular inspections to ensure compliance with local housing codes and zoning restrictions.

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 beaches, water sports, and seasonal 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 Virginia Beach. The Western Branch area near the Elizabeth River offers a quieter alternative for families and groups seeking proximity to both Norfolk's attractions and Virginia Beach's entertainment districts. The South Norfolk historic district appeals to cultural tourists interested in Civil War history and heritage tourism, particularly during spring and fall months when historical events and festivals drive demand. These areas benefit from Chesapeake's strategic location between Virginia Beach's tourism infrastructure and Norfolk's business centers, creating year-round rental demand from diverse guest segments.

In Chesapeake, Virginia, Airbnb hosts are subject to both state and local lodging taxes. The Virginia state transient occupancy tax is 5.3% on stays less than 90 days, which Airbnb automatically collects and remits to the state for most bookings. Additionally, Chesapeake imposes a local transient occupancy tax of 5% on short-term rental accommodations, bringing the total tax burden to approximately 10.3%. The local tax must be collected by hosts and remitted quarterly to the City of Chesapeake's Department of Finance, with returns due by the last day of the month following each quarter (April 30, July 31, October 31, and January 31). Hosts are required to register with the city and obtain a transient occupancy tax certificate before operating. Exemptions typically include stays of 90 days or longer, which are considered permanent residency rather than transient occupancy, and accommodations provided to certain government employees on official business. Failure to collect and remit these taxes can result in penalties and interest charges, and hosts should maintain detailed records of all bookings and tax collections for audit purposes.

Starting an Airbnb in Chesapeake, Virginia requires approximately $380,000-$420,000 in total initial investment. Property purchase costs around $350,000 based on median home prices in the area as of 2023. Furnishing a 3-bedroom property typically costs $15,000-$25,000 including furniture, appliances, linens, and décor to create an attractive rental space. Initial setup expenses including professional photography, listing creation, and basic renovations run $3,000-$5,000. Permits and fees in Chesapeake include business license ($50), short-term rental permit ($200), and potential zoning compliance costs totaling approximately $500-$1,000. Insurance for short-term rentals costs $1,200-$2,000 annually, with many hosts using companies like Proper Insurance or CBIZ. 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), maintenance reserves ($300/month), property management software like Airbnb or VRBO fees (3% of bookings), and marketing expenses total approximately $4,000-$6,000, assuming 60-70% occupancy rates typical for the Hampton Roads market.

Airbnb properties in Chesapeake, Virginia typically generate annual revenues between $15,000-$35,000 for entire homes, with average daily rates ranging from $85-$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-$80 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 45-55%, 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 4.8% cash-on-cash return, making Chesapeake a moderately profitable market for investors who understand seasonal demand patterns and military housing allowance rates.

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 recovery and profitability generally occurs within 18-24 months for well-positioned properties, assuming 60-70% occupancy rates throughout the year. The market benefits from steady demand from military personnel, business travelers visiting the Hampton Roads area, and tourists exploring the Chesapeake Bay region, with peak seasons during summer months and military deployment cycles driving consistent bookings and revenue streams for property investors.

STRSearch leads the market in Airbnb investment property analysis nationwide including Chesapeake, Virginia. Local real estate agents specializing in short-term rental investments in Chesapeake include Keller Williams Realty agents like Sarah Mitchell and Hampton Roads Realty's investment division led by Mark Thompson. RedAwning (founded 2009) and Awning (established 2017) provide national Airbnb property investment services covering the Virginia Beach-Norfolk metropolitan area. Local property management companies like Coastal Virginia Vacation Rentals and Tidewater Property Solutions offer turnkey Airbnb setup services. National platforms include Mashvisor for market analysis, BiggerPockets for investor networking, and AirDNA for revenue projections. Regional firms such as Virginia Beach Investment Properties and Norfolk Real Estate Investors Group provide market expertise. Roofstock and Arrived Homes offer online platforms for purchasing rental properties, while local mortgage brokers like Atlantic Bay Mortgage Group specialize in investment property financing. Property management services include RedAwning, AvantStay, and local companies like Hampton Roads Short Term Rentals that handle everything from guest communication to maintenance for Chesapeake Airbnb properties.