Chesapeake, VA Airbnb Market Data, Statistics, and Occupancy Rates

Chesapeake Short-Term Rental Market Overview

Chesapeake, VA is a compact but growing short-term rental market with just 50 active Airbnb listings and a striking 96% year-over-year increase in supply — a signal that investors are catching on. Average annual revenue sits at $27,995 against a $599,475 average home value, and occupancy of 38% outpaces the Virginia state average of 34%. With an ADR of $143 — well below the $339 state average — the market caters to value-conscious travelers, creating a distinct niche within the Hampton Roads region.

Key Market Statistics

According to Rabbu market data, the Chesapeake short-term rental market shows:

Data sources: Rabbu proprietary analytics as of Apr, 27 2026 and Zillow Home Value Index (ZHVI) as of Apr, 27 2026.

Why Investors Consider Chesapeake

Chesapeake presents a balanced opportunity where moderate revenue, rising demand, and affordable entry relative to coastal Virginia peers make it compelling for investors seeking steady returns without premium price tags.

Expert Market Assessment

"With an ROI score of 59 out of 100 — categorized as an 'Attractive Opportunity' — Chesapeake offers a solid entry point for investors who prioritize affordability and emerging demand over top-line revenue. Seasonality is pronounced: July peaks at $4,224 in average monthly revenue while January bottoms out near $1,178, creating roughly a 3.6x swing that investors must budget around. The supply-demand balance and occupancy stability both sit at average levels, so returns hinge on choosing the right property size and managing off-season pricing carefully. Three-bedroom listings stand out as the clear revenue leaders, making them the most attractive configuration for maximizing cash flow in this market."

— Rabbu Market Analysis Team

Key Airbnb Metrics & Trends in Chesapeake

Average revenue by month in Chesapeake

Chesapeake exhibits strong seasonality, with July delivering peak revenue of $4,224 — more than 3.5 times the January low of $1,178. Investors should plan for a concentrated earning window from June through August, which accounts for a disproportionate share of annual income, and budget conservatively for the November–February slowdown.

Active Airbnb listings by property size in Chesapeake

One-bedroom listings dominate supply with 21 of the 50 active properties, followed by 16 three-bedrooms and just 9 two-bedrooms. The relatively thin two-bedroom segment could represent an opportunity gap, though investors should weigh this against the size category's lower occupancy rate of 25%.

Average daily rate (ADR) by property size in Chesapeake

ADR rises steadily with size — from $85 for one-bedrooms to $166 for two-bedrooms and $193 for three-bedrooms. The jump from one to two bedrooms is particularly steep at nearly double the rate, suggesting a strong pricing premium for the added space.

Average RevPAN by property size in Chesapeake

Three-bedroom properties deliver the strongest RevPAN at $93, more than double the two-bedroom figure of $41 and nearly triple the one-bedroom's $34. This gap makes three-bedrooms the clear leader in revenue efficiency after factoring in both nightly rates and occupancy.

Average occupancy rates by property size in Chesapeake

Three-bedroom listings lead occupancy at 48%, followed by one-bedrooms at 41%, while two-bedrooms lag considerably at just 25%. For investors prioritizing consistent booking activity and cash-flow stability, the three-bedroom category offers the best combination of high occupancy and premium pricing.

Average monthly revenue by property size in Chesapeake

Monthly revenue ranges from $1,279 for one-bedrooms up to $3,502 for three-bedroom properties, with two-bedrooms landing at $2,425. The roughly $2,200 gap between the smallest and largest configurations underscores how meaningful the right property size is to cash-flow outcomes in this market.

Average annual revenue by property size in Chesapeake

Three-bedroom properties generate an average of $42,028 annually — nearly 2.75 times the $15,349 earned by one-bedroom listings and about 44% more than two-bedrooms at $29,103. For investors eyeing the strongest return potential in Chesapeake, three-bedroom configurations offer the most compelling revenue profile relative to operational effort.

Most common amenities for Airbnb listings in Chesapeake

Parking (100%), a kitchen (98%), and in-unit laundry (92% washer, 90% dryer) are virtually standard across Chesapeake listings, signaling that guests expect a home-like, self-sufficient experience. Workspaces appear in 70% of listings and backyards in 76%, suggesting demand from remote workers and families — while premium features like pools (10%) and hot tubs (4%) remain rare differentiators.

Understanding Chesapeake's ROI Score: 59/100

Rabbu's ROI Score is a proprietary metric that evaluates short-term rental investment potential based on multiple factors.

How the ROI Score is Calculated

What This Means for Investors

Chesapeake's ROI score of 59 out of 100 places it in the 'Attractive Opportunity' band, reflecting average revenue-to-price and occupancy stability metrics paired with an above-average market growth trend. The rapid supply expansion (96% year-over-year) hasn't yet outpaced demand, but investors should monitor this balance as new listings enter the market. Pairing this data with thorough local regulatory research and a focus on three-bedroom properties — the top revenue performers — will help maximize the opportunity this score suggests.

Short-Term Rental Regulations in Chesapeake

Understanding local STR regulations is essential before investing in Chesapeake. Here's the current regulatory landscape:

Permit Requirements

The City of Chesapeake and the Commonwealth of Virginia may require short-term rental operators to obtain permits, register their property, or secure a business license before listing. Investors should verify current requirements directly with Chesapeake's planning and zoning department, as local rules can evolve quickly in growing markets.

Key Restrictions

Common restrictions in Virginia cities like Chesapeake can include occupancy limits tied to bedroom count, minimum-stay requirements in certain residential zones, noise ordinances, parking mandates, and HOA covenants that may prohibit or limit short-term rentals. Prospective hosts should review their property's zoning classification and any homeowner association rules before committing to a purchase.

Tax Obligations

Short-term rental operators in Virginia are generally subject to state and local transient occupancy taxes, and the City of Chesapeake may impose additional lodging or tourism-related levies. Platforms like Airbnb often collect and remit some of these taxes on behalf of hosts, but operators should confirm their full tax obligations with a local accountant or the city's revenue office.

Regulations subject to change. Always verify with local authorities before purchasing. A Rabbu partner agent specializing in Chesapeake can provide current regulatory guidance.

Future Outlook & Long-Term Forecast

"The rapid growth in active listings (96% year-over-year) suggests mounting investor interest, but Chesapeake's above-average market growth trend indicates demand is keeping pace for now. Over the next 12–18 months, we estimate occupancy could stabilize in the 36–40% range as new supply is absorbed, with ADR potentially ticking up 2–4% as hosts refine pricing for summer peaks. Three-bedroom properties, which already command a $93 RevPAN, are well-positioned to capture family and group travel during the June–August corridor. Investors entering now should plan conservatively for winter months when revenue dips below $1,200, but the strong summer ceiling offers meaningful upside."

— Rabbu Market Analysis Team

Frequently asked questions about Airbnb in Chesapeake, VA

What is the average Airbnb occupancy rate in Chesapeake?

The average occupancy rate for Airbnb listings in Chesapeake is currently 38%, which edges out the Virginia state average of 34%. Occupancy varies significantly by property size — three-bedroom listings lead at 48%, while two-bedroom units trail at 25%. Seasonality also plays a role, with summer months driving the highest demand and winter months seeing softer bookings.

How much do Airbnb hosts make in Chesapeake?

Based on trailing 12-month booking data, Airbnb hosts in Chesapeake earn an average of $2,332 per month and approximately $27,995 per year. Earnings vary considerably by property size: one-bedroom listings average $15,349 annually, two-bedrooms bring in about $29,103, and three-bedroom properties lead at $42,028 per year. Individual results will depend on factors like property quality, location within the city, amenities offered, and pricing strategy.

Is Chesapeake a good market for Airbnb investment?

Chesapeake earns a Rabbu ROI score of 59 out of 100, placing it in the 'Attractive Opportunity' category. The market benefits from above-average growth trends and occupancy that beats the state average, though revenue-to-price ratios are in line with — rather than ahead of — broader norms. With average home values around $599,475 and annual revenue near $28,000, investors should target higher-earning three-bedroom properties and manage seasonality carefully to achieve the best returns.

What is the average daily rate (ADR) for Airbnb in Chesapeake?

The average daily rate in Chesapeake is $143, which is significantly below the Virginia state average of $339. This reflects Chesapeake's position as a value-oriented market compared to nearby coastal destinations. ADR scales meaningfully with size: one-bedroom listings average $85, two-bedrooms come in at $166, and three-bedroom properties command $193 per night.

Are short-term rentals legal in Chesapeake?

Short-term rentals do operate in Chesapeake, VA, with approximately 50 active Airbnb listings currently in the market. However, local regulations — including permits, zoning requirements, and potential restrictions — can change, so prospective investors should check directly with the City of Chesapeake's planning and zoning office and review any applicable HOA rules before purchasing a property for short-term rental use.

When is peak season for Airbnb in Chesapeake?

Peak season in Chesapeake runs from June through August, with July topping out at $4,224 in average monthly revenue and August close behind at $3,914. The shoulder months of April, May, and September still perform reasonably well in the $2,100–$2,500 range. Winter months from November through February are the slowest period, with revenue dropping to the $1,178–$1,484 range.

How many Airbnbs are there in Chesapeake?

There are currently 50 active Airbnb listings in Chesapeake, a relatively small supply pool that has nearly doubled over the past year with 96% year-over-year growth. Of these, one-bedroom listings make up the largest share at 21 units, followed by 16 three-bedroom and 9 two-bedroom properties.

How is Airbnb revenue calculated in Chesapeake?

The annual and monthly revenue figures for Chesapeake are derived from the trailing 12 months of historical booking performance for active comparable Airbnb listings in the market — they are not forward-looking projections. We average each comparable listing's actual revenue per available night (RevPAN) by month over the past year, remove regional outliers, and roll the results up to a market-level historical average. Because each month uses its own historical performance, the figures naturally reflect seasonal peaks and slower months. Individual results can vary based on property quality, pricing strategy, and operational management.

About Rabbu Market Data

Rabbu provides Airbnb and short-term rental market data and statistics across the United States. Our mission is to empower investors with accurate insights and easy-to-use tools, so they can confidently identify and act on the best opportunities in the Airbnb market.

What this data includes

• Regularly updated active Airbnb and STR listing counts for Chesapeake and comparable Virginia markets
• Average daily rate, occupancy, and RevPAN metrics by property size and time period
• Historical monthly and annual revenue figures based on trailing 12-month booking data
• Amenity prevalence data across active listings to identify guest expectations and competitive gaps
• Home value estimates sourced from the Zillow Home Value Index (ZHVI) for investment analysis

Sources and disclaimers

Rabbu proprietary analytics as of Apr, 27 2026 and Zillow Home Value Index (ZHVI) as of Apr, 27 2026. Revenue projections are estimates based on comparable properties and do not guarantee future performance. Data reflects trailing 12-month performance as of April 2026 and may not capture very recent market shifts. Local regulations, tax obligations, and permit requirements can change; always verify with municipal authorities before investing.