Chestertown, MD Airbnb Market Data, Statistics, and Occupancy Rates

Chestertown Short-Term Rental Market Overview

Chestertown, MD presents an attractive short-term rental opportunity on Maryland's Eastern Shore, earning an ROI score of 62 out of 100. With just 42 active Airbnb listings and average annual revenue of $48,318 per property, the market remains small and relatively uncrowded. A strong 94% year-over-year listing growth rate signals rising investor interest, while the average daily rate of $382 edges above the $368 state average — suggesting guests are willing to pay a premium for this waterfront community's charm.

Key Market Statistics

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

Data sources: Rabbu proprietary analytics as of Apr, 27 2026 and Zillow Home Value Index (ZHVI) as of Mar, 17 2026.

Why Investors Consider Chestertown

Chestertown appeals to investors seeking a small, growing Eastern Shore market where limited supply and premium nightly rates create a favorable revenue-to-price dynamic.

Expert Market Assessment

"Chestertown represents a moderate-to-attractive opportunity for STR investors who understand its seasonal rhythm. Revenue swings dramatically — from a February low of $1,425 to a July peak of $7,291 — so cash-flow planning around a roughly five-month high season (May through September) is essential. The market's compact size and above-average growth trend suggest demand is outpacing supply for now, though the 26% occupancy rate indicates plenty of available nights still go unbooked. Investors who target 3-bedroom properties may find the best balance of revenue potential ($52,226 annually) and manageable acquisition costs."

— Rabbu Market Analysis Team

Key Airbnb Metrics & Trends in Chestertown

Average revenue by month in Chestertown

Chestertown's revenue is heavily seasonal, peaking at $7,291 in July and bottoming out at $1,425 in February — a spread of nearly $5,900. The core earning season runs May through September, accounting for the bulk of annual income, so investors should plan cash reserves to cover the quieter November–March stretch.

Active Airbnb listings by property size in Chestertown

Three-bedroom homes lead the supply count with 11 listings, followed closely by 2-bedrooms (10) and 5-bedrooms (8), while 1-bedroom units are the scarcest at just 5. The absence of 4-bedroom listings in the data could signal a gap in supply that savvy investors might fill to capture mid-size group demand.

Average daily rate (ADR) by property size in Chestertown

ADR climbs steeply with property size, from $156 for 1-bedroom units to $630 for 5-bedroom homes — a 4× increase. The jump from 2-bedrooms ($218) to 3-bedrooms ($368) is particularly notable, suggesting that adding a third bedroom unlocks a meaningful pricing premium.

Average RevPAN by property size in Chestertown

Three-bedroom properties deliver the highest RevPAN at $93, slightly outperforming 5-bedroom homes ($86) despite their lower nightly rate. This indicates that 3-bedroom units achieve a stronger combination of rate and occupancy, making them an efficient choice for revenue per available night.

Average occupancy rates by property size in Chestertown

Occupancy drops sharply as property size increases — 1-bedrooms lead at 33%, 2-bedrooms hold at 30%, 3-bedrooms sit at 25%, and 5-bedrooms trail at just 14%. Investors eyeing larger properties should weigh the higher nightly rate against the significantly fewer booked nights, which can create cash-flow variability.

Average monthly revenue by property size in Chestertown

Five-bedroom listings top monthly revenue at $5,465, while 3-bedroom properties earn $4,352 and remain the sweet spot when factoring in lower acquisition and operating costs. One-bedroom units generate just $2,336 per month, making them less compelling for investors seeking meaningful cash flow.

Average annual revenue by property size in Chestertown

Annual revenue ranges from $28,038 for 1-bedroom listings to $65,582 for 5-bedroom properties, with 3-bedrooms at $52,226 offering a strong middle ground. When measured against likely purchase prices, the 3-bedroom tier may provide the most attractive yield given its higher RevPAN and lower capital outlay compared to 5-bedroom homes.

Most common amenities for Airbnb listings in Chestertown

Parking is universal at 100% of listings, and kitchen (95%), washer (88%), and dryer (86%) are near-standard — guests in Chestertown clearly expect home-like conveniences. Outdoor features like patios (74%), outdoor furniture (74%), and backyards (71%) are also widespread, while waterfront access (31%) and pet-friendliness (41%) serve as differentiators that could help a listing stand out.

Understanding Chestertown's ROI Score: 62/100

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

Chestertown's ROI score of 62 out of 100 places it in the "Attractive Opportunity" band, reflecting average revenue-to-price and occupancy stability metrics alongside an above-average market growth trend. The balanced supply/demand dynamic and rising investor interest suggest the market hasn't yet been saturated, which bodes well for early movers. Investors should pair this score with local regulatory research and a realistic seasonal cash-flow model to determine whether the opportunity fits their portfolio goals.

Short-Term Rental Regulations in Chestertown

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

Permit Requirements

Operators in Chestertown, MD should verify whether a short-term rental permit or business registration is required through the Town of Chestertown and Kent County offices. Maryland does not impose a statewide STR licensing framework, so local requirements can vary and should be confirmed directly with municipal authorities.

Key Restrictions

Common restrictions in similar Maryland markets include occupancy limits, minimum-stay requirements, noise ordinances, parking mandates, and potential HOA restrictions for properties within planned communities. Investors should also check whether there are any caps on the number of STR permits issued in the area and review zoning designations before purchasing.

Tax Obligations

Short-term rental operators in Maryland are typically subject to state sales tax, county lodging or transient occupancy taxes, and potentially a local tourism tax. Major booking platforms often collect and remit some of these taxes on behalf of hosts, but operators should confirm their full obligation with the Maryland Comptroller's office and Kent County.

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

Future Outlook & Long-Term Forecast

"Over the next 12–18 months, Chestertown's STR market is likely to benefit from continued above-average growth trends and steady seasonal demand driven by summer and early-fall travel. Revenue could see modest increases of 2–5% as the market matures, though occupancy — currently at 26% versus the 35% state average — may need to climb before returns feel robust year-round. Investors should anticipate strong cash flow from May through September, with softer winter months pulling annual averages down. Pairing a competitive pricing strategy with high-quality amenities could help capture a larger share of shoulder-season bookings."

— Rabbu Market Analysis Team

Frequently asked questions about Airbnb in Chestertown, MD

What is the average Airbnb occupancy rate in Chestertown?

The average occupancy rate for Airbnb listings in Chestertown is currently 26%, which falls below the Maryland state average of 35%. Occupancy varies significantly by property size — 1-bedroom units lead at 33%, while larger 5-bedroom homes average just 14%. The lower overall rate reflects Chestertown's seasonal demand profile, with most bookings concentrated in the warmer months.

How much do Airbnb hosts make in Chestertown?

Based on trailing 12-month data, the average Airbnb host in Chestertown earns approximately $4,026 per month, which translates to about $48,318 annually. Earnings vary considerably by property size: 5-bedroom listings average $65,582 per year, while 1-bedroom units bring in around $28,038. Peak summer months like July can generate over $7,200 in a single month, so much of the annual total is concentrated in the May–September window.

Is Chestertown a good market for Airbnb investment?

Chestertown scores a 62 out of 100 on Rabbu's ROI Score, placing it in the "Attractive Opportunity" category. The market benefits from above-average growth trends and a daily rate ($382) that exceeds the state average. However, the relatively low occupancy rate and pronounced seasonality mean investors should plan for slower winter months. Properties with waterfront access or 3+ bedrooms tend to perform best and may offer the strongest return potential.

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

The current average daily rate in Chestertown is $382, slightly above the Maryland state average of $368. ADR scales significantly with property size — 1-bedroom listings average $156 per night, 2-bedrooms sit at $218, 3-bedrooms reach $368, and 5-bedroom homes command $630 per night. This pricing structure rewards investors who can offer larger, well-appointed properties.

Are short-term rentals legal in Chestertown?

Short-term rentals do operate in Chestertown, MD, but specific permit requirements and local regulations should be verified directly with the Town of Chestertown and Kent County. Maryland does not have a statewide STR licensing mandate, so rules can vary at the local level. Prospective investors should also review zoning, HOA rules, and any applicable tax obligations before listing a property.

When is peak season for Airbnb in Chestertown?

Peak season in Chestertown runs from June through August, with July delivering the highest average monthly revenue at $7,291. The strong season extends into May ($4,862) and September ($5,536), giving hosts a roughly five-month high-earning window. Winter months are considerably softer — February averages just $1,425 — so investors should budget accordingly for the off-season.

How many Airbnbs are there in Chestertown?

As of April 2026, there are 42 active Airbnb listings in Chestertown. The supply is distributed across property sizes, with 3-bedroom homes (11 listings) and 2-bedroom units (10 listings) making up the largest share. Year-over-year listing growth of 94% shows the market is expanding quickly, though the overall count remains small compared to larger Maryland destinations.

How is Airbnb revenue calculated in Chestertown?

The annual and monthly revenue figures shown for Chestertown 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 remaining data up to a market-level historical average. Because each month uses its own historical performance, the figures naturally reflect seasonal peaks and slower periods. Individual results can vary based on property quality, pricing strategy, and how actively you manage your listing.

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 the Chestertown market
• Average daily rate, occupancy, and RevPAN metrics across property sizes
• Monthly and annual revenue trends based on trailing 12-month booking data
• Home value estimates sourced from Zillow Home Value Index (ZHVI)
• Popular amenity prevalence across active listings to inform property setup decisions

Sources and disclaimers

Rabbu proprietary analytics as of Apr, 27 2026 and Zillow Home Value Index (ZHVI) as of Mar, 17 2026. Revenue projections are estimates based on comparable properties and do not guarantee future performance. Data reflects trailing performance and market conditions as of the dates noted; future results may differ due to regulatory changes, economic shifts, or competitive dynamics. Local STR regulations vary and should be independently verified with municipal and county authorities before investing.