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

Chestertown Short-Term Rental Market Overview

Chestertown, NY, is a small Adirondack-region market with just 48 active Airbnb listings, offering investors a niche opportunity driven by seasonal outdoor recreation and lake access. Average annual revenue comes in at $38,739, with a sharp summer peak that pushes August earnings above $8,300 — more than six times the slowest month. While the average daily rate of $356 sits slightly below the New York state average, low occupancy at 27% signals a heavily seasonal demand pattern that requires careful financial planning. With an ROI score of 54 out of 100, the market rewards selective deal sourcing rather than blanket investment.

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 Apr, 27 2026.

Why Investors Consider Chestertown

Investors look at Chestertown for its Adirondack vacation appeal and premium summer revenue potential, balanced against heavily seasonal demand and rising competition.

Expert Market Assessment

"Chestertown represents a competitive but narrowly seasonal opportunity for STR investors. Revenue is heavily concentrated in the summer months — July and August alone account for roughly 40% of annual earnings — while the November-through-April stretch sees monthly revenues dip below $2,700. The below-average occupancy rate of 27% (versus 40% statewide) reflects this seasonality and the rapid expansion of supply. Investors who target larger properties with lake access and price strategically during peak season stand the best chance of achieving meaningful returns in this Adirondack market."

— Rabbu Market Analysis Team

Key Airbnb Metrics & Trends in Chestertown

Average revenue by month in Chestertown

Revenue in Chestertown is sharply seasonal, peaking at $8,397 in August and bottoming out at $1,285 in April — a spread of over $7,100. The June-through-September window generates the vast majority of annual income, so investors should budget for lean months from late fall through early spring.

Active Airbnb listings by property size in Chestertown

Three-bedroom properties dominate supply with 18 of the 48 active listings, followed by 4-bedrooms (13) and 2-bedrooms (12). The absence of 1-bedroom and 5+ bedroom data suggests those segments are either very thin or nonexistent, which could represent niches worth exploring depending on demand.

Average daily rate (ADR) by property size in Chestertown

ADR scales steeply with size in Chestertown: 2-bedroom listings average $240/night, 3-bedrooms reach $317, and 4-bedroom properties command $490. The jump from 3 to 4 bedrooms represents a 55% rate premium, suggesting strong guest willingness to pay for larger vacation homes.

Average RevPAN by property size in Chestertown

RevPAN increases steadily with property size, from $70 for 2-bedrooms to $83 for 3-bedrooms and $119 for 4-bedroom listings. The 4-bedroom segment delivers nearly 70% more revenue per available night than 2-bedrooms, making it the clear leader in yield efficiency despite slightly lower occupancy.

Average occupancy rates by property size in Chestertown

Occupancy rates are modest across all sizes, ranging from 29% for 2-bedrooms down to 24% for 4-bedroom properties. Smaller units fill marginally more often, but the gap is narrow enough that the higher nightly rates on larger properties more than compensate for the occupancy difference.

Average monthly revenue by property size in Chestertown

Four-bedroom properties lead monthly revenue at $5,484 — more than double the $2,621 earned by 3-bedroom listings and well above the $2,186 for 2-bedrooms. This gap underscores how larger properties capture disproportionate revenue in a vacation-driven market like Chestertown.

Average annual revenue by property size in Chestertown

Annual revenue tells a compelling story for larger formats: 4-bedroom listings average $65,817 per year, roughly 2.5 times the $26,237 earned by 2-bedroom properties and more than double the $31,454 for 3-bedrooms. Investors targeting higher gross revenue should focus on 4-bedroom homes, though acquisition costs and carrying expenses during off-season months need careful consideration.

Most common amenities for Airbnb listings in Chestertown

Kitchens (98%), parking (96%), and BBQ grills (94%) are near-universal, reflecting guest expectations for self-sufficient vacation stays. Lake access appears in 67% of listings and waterfront in 35%, signaling that proximity to water is a key differentiator — while hot tubs, offered by just 25% of hosts, could provide a competitive edge for properties that add them.

Understanding Chestertown's ROI Score: 54/100

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 54 out of 100 places it in the 'Competitive Opportunity' band, meaning the market has genuine appeal but demands disciplined deal selection. The revenue-to-price ratio and supply/demand balance both rate as average, while occupancy stability and market growth trend fall below average — reflecting the sharp seasonality and rapid supply expansion that define this Adirondack market. Pairing these metrics with thorough local regulatory research and conservative off-season cash-flow modeling will help investors identify properties that can still deliver solid returns.

Short-Term Rental Regulations in Chestertown

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

Permit Requirements

Short-term rental operators in Chestertown, NY, should check with the Town of Chestertown and Warren County for any permit or registration requirements before listing a property. New York State does not impose a statewide STR permit, so local rules are the primary consideration.

Key Restrictions

Common STR restrictions that may apply include occupancy limits, minimum stay requirements, noise ordinances, and parking regulations. Investors should also review any HOA covenants or deed restrictions on their specific property, as these can impose additional limitations beyond municipal rules.

Tax Obligations

Short-term rental hosts in New York are generally subject to state and local sales tax, as well as any applicable county occupancy or lodging taxes. Platforms like Airbnb often collect and remit state sales tax on behalf of hosts, but investors should confirm their full tax obligations with a local accountant or the Warren County treasurer's office.

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 performance is expected to remain tightly tied to summer tourism, with July and August continuing to generate the lion's share of annual revenue. Listing supply has grown significantly — 150% year over year — which could put downward pressure on occupancy and rates unless demand keeps pace. ADR may hold steady or soften by 1–3% as competition intensifies, and investors should plan for occupancy in the 25–30% range on an annualized basis. Properties with lake access or waterfront positioning will likely outperform the broader market average during peak months."

— Rabbu Market Analysis Team

Frequently asked questions about Airbnb in Chestertown, NY

What is the average Airbnb occupancy rate in Chestertown?

The average occupancy rate for Airbnb listings in Chestertown is currently 27%, which is below the New York state average of 40%. This reflects the market's heavy seasonal demand — summer months drive the bulk of bookings, while the off-season sees significantly lower activity. Two-bedroom properties tend to fill slightly better at 29%, while larger 4-bedroom homes average around 24%.

How much do Airbnb hosts make in Chestertown?

On average, Airbnb hosts in Chestertown earn approximately $3,228 per month and $38,739 per year based on trailing 12-month data. However, there's a wide range by property size: 2-bedroom listings average $26,237 annually, 3-bedrooms bring in about $31,454, and 4-bedroom properties lead at $65,817 per year. Monthly earnings vary dramatically by season, with August topping out near $8,397 and April dipping to roughly $1,285.

Is Chestertown a good market for Airbnb investment?

Chestertown earns an ROI score of 54 out of 100, placing it in the 'Competitive Opportunity' category. The market offers strong summer revenue potential and premium nightly rates for larger properties, but investors face below-average occupancy stability and a rapidly growing supply of listings. Success here typically depends on targeting the right property type — particularly 4-bedroom homes with lake access — and pricing strategically around peak summer demand. Thorough deal sourcing and conservative off-season budgeting are important.

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

The average daily rate in Chestertown is $356, just below the New York state average of $381. ADR scales significantly with property size: 2-bedroom listings average $240 per night, 3-bedrooms come in at $317, and 4-bedroom properties command a premium at $490 per night.

Are short-term rentals legal in Chestertown?

Short-term rentals can be operated in Chestertown, NY, though investors should verify any local permit, registration, or zoning requirements with the Town of Chestertown and Warren County. Regulations can change, so it's advisable to consult local authorities or a real estate attorney before purchasing a property specifically for STR use.

When is peak season for Airbnb in Chestertown?

Peak season in Chestertown runs from late June through August, aligning with Adirondack summer tourism. August is the single highest-earning month, with average revenue of $8,397, followed by July at $6,968. Revenue drops sharply in the shoulder months — September averages $3,347 and June $3,312 — before falling to off-season lows in the $1,200–$1,700 range from March through April.

How many Airbnbs are there in Chestertown?

As of April 2026, there are 48 active Airbnb listings in Chestertown. The supply is concentrated in mid-size properties: 18 are 3-bedroom listings, 13 are 4-bedrooms, and 12 are 2-bedrooms. Notably, listing supply has grown 150% year over year, so the competitive landscape is shifting quickly.

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. Rabbu averages each comparable listing's actual revenue per available night (RevPAN) by month over the past year, removes regional outliers, and rolls the remainder up to a market-level historical average. This approach anchors the figures to what hosts have actually earned recently while naturally reflecting seasonal peaks and slower months, since each month uses its own historical performance data. Individual results can vary based on property quality, pricing strategy, location within Chestertown, 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 by market and property size
• Average daily rate, occupancy, and RevPAN metrics with state-level benchmarks
• Monthly and annual revenue trends based on trailing 12-month booking data
• Property-level amenity prevalence across active listings
• Home value estimates sourced from the Zillow Home Value Index (ZHVI)

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 historical averages as of April 2026 and may not capture very recent market shifts. Local regulations, HOA rules, and tax obligations vary and should be independently verified before making any investment decision.