In Chestertown, New York, the average short-term rental earns $37.7K per year and books at a $301 average daily rate.
The average active short-term rental in Chestertown earns $37.7K a year, booking at an average daily rate of $301 per night. Both figures are trailing-twelve-month averages across every active Chestertown listing on Airbnb, Vrbo, and Booking.com.
From August 2025 to August 2026, Chestertown short-term rental revenue is up 42.4% and the average daily rate is down 10.0%.
Chestertown's Revenue Growth subscore is 65 out of 100, one of five inputs to its overall Market Score of 54.
Revenue Growth is the year-over-year change in RevPAR (revenue per available rental), counting only properties booked in both periods so new and delisted listings can't skew it. Chestertown's RevPAR is down 15.5% from August 2025 to August 2026.
It is benchmarked against other short-term rental markets in the same country with at least 15 active listings.
Market-level averages hide wide variation. Here's how to go deeper in the app:
Key definitions

How a typical listing's monthly revenue rises and falls across the year.
How nightly rates move month to month, with entire-place, pro-managed, and luxury segment cuts.
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Frequently asked
The average active Chestertown short-term rental earns $37.7K a year.
Chestertown's market-wide average daily rate is $301 per booked night.
Chestertown's average daily rate is down 10.0% from August 2025 to August 2026, now $301 per booked night.
Chestertown short-term rental revenue is up 42.4% from August 2025 to August 2026, averaging $37.7K per active listing.
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