Chestertown, New York Short-Term Rental Market
Chestertown, NY STRs averaged $235/night in April 2026 in a dual-season Adirondacks market where summer and winter both drive strong demand.
Quick Answer: Chestertown, New York is an active short-term rental market. average occupancy in the Adirondacks market area is 52%. average monthly revenue in the Adirondacks market area is $4,101. average daily rate in the Adirondacks market area is $359. the top operator in the Adirondacks market area is Evolve with 166 listings. market score is 57/100 (grade C).
Market data reflects the Adirondacks regional market, which includes Chestertown. Regulations, taxes, and permit details below are specific to Chestertown.
Market Score Breakdown
Five dimensions StaySTRA evaluates per market.
Market Overview
Chestertown is a small hamlet (population 586) in the Town of Chester, Warren County, New York, situated in the southeastern Adirondacks about 20 minutes from Gore Mountain ski resort and adjacent to Loon Lake. It functions as a year-round outdoor recreation destination, drawing summer visitors for lake activities and winter visitors for skiing, with two distinct demand peaks rather than a single summer season. The market draws travelers from the broader Lake George and Adirondacks region.
The latest data month is April 2026, the shoulder period between ski and summer seasons, when occupancy stood at 24.85% and ADR was $234.81, generating $58.34 in RevPAR and $1,956 average monthly revenue. April is historically the market’s weakest month (35.7% average occupancy across all years), so the April snapshot understates full-year potential. Year-over-year, April 2026 occupancy declined 23.85% from April 2025, a notable drop; ADR rose 4.3% and revenue fell 13.4%. The 6,137 total listing records break down by bedroom size: 1-bedroom (1,392), 2-bedroom (1,503), 3-bedroom (1,671), 4-bedroom (910), and 5-bedroom or larger (654), skewed toward larger group-oriented properties. By listing type, entire-place units dominate at 5,894, with private rooms at 241 and shared rooms at 2. Channel distribution shows 2,751 listings on both Airbnb and VRBO, 2,635 Airbnb-only, and 751 VRBO-only. Market investability score is 94.3 out of 100, the highest in this batch.
Seasonal Patterns
| Month | Occupancy |
|---|---|
| Jan | 39% |
| Feb | 51% |
| Mar | 33% |
| Apr | 36% |
| May | 44% |
| Jun | 53% |
| Jul | 70% |
| Aug | 69% |
| Sep | 42% |
| Oct | 42% |
| Nov | 32% |
| Dec | 47% |
Month-by-month nightly rates and revenue figures for Chestertown are available to StaySTRA Pro members. Unlock with StaySTRA Pro or analyze a specific address free.
Top Short-Term Rental Operators in Adirondacks market area
Ranked by total active listings. Useful for understanding the competitive landscape. Operator data is published for the Adirondacks market as a whole, which includes Chestertown, so these counts are not Chestertown-only figures.
| # | Operator | Listings | Reviews | Rating |
|---|---|---|---|---|
| 1 | Evolve | 166 | 6,967 | ★ 4.77 |
| 2 | Adirondack By Owner | 97 | 3,146 | ★ 4.83 |
| 3 | Vacasa | 73 | 2,151 | ★ 4.58 |
| 4 | Northern Living | 66 | 2,312 | ★ 4.85 |
| 5 | Rocky Point Properties | 57 | 530 | ★ 4.82 |
What Kind of STR Should I Buy in Chestertown?
Revenue and nightly-rate breakdowns by bedroom count, property tier, and dwelling type for Chestertown are available to StaySTRA Pro members. Unlock with StaySTRA Pro or analyze a specific address free.
Booking Channel Mix
Distribution of bookings across major STR platforms.
| Channel | Share |
|---|---|
| airbnb | 42.9% |
| vrbo | 12.2% |
| both | 44.8% |
Home Value Trends (Chestertown)
Typical home values, median sale prices, and the 10-year price trend for Chestertown are available to StaySTRA Pro members. Unlock with StaySTRA Pro or analyze a specific address free.
Booking Insights
Booking-window and length-of-stay analysis for Chestertown — how far ahead guests book and how to price around it — is available to StaySTRA Pro members. Unlock with StaySTRA Pro or analyze a specific address free.
Short-Term Rental Regulations
Short-term rentals in the Town of Chester (which encompasses Chestertown hamlet) are permitted but regulated under a Short-Term Rental Local Law adopted in 2022. Operators must obtain a Short-Term Rental Permit from the Planning and Zoning / Building Department before renting. Applications opened October 1, 2023, and permits require annual renewal along with safety inspections. Applications filed on or after January 1, 2024 incur an additional after-the-fact surcharge of $100. The base permit fee is set by Town Board resolution and was not published online at the time of the area profile update; confirm directly with the Planning and Zoning Office at 518-494-7369.
At the county level, all STR owners in Warren County must register with the County Treasurer and collect and remit the county’s 4% occupancy tax per guest stay, in effect since September 1, 2020. This occupancy tax rate is confirmed in the area profile. Failure to obtain a town permit can result in fines of approximately $500 to $3,000 per violation; the county can impose penalties of up to 5% plus interest for late or unpaid occupancy tax. No owner-occupancy or primary-residence requirement was confirmed. Enforcement is rated moderate. No major recent changes to the regulatory framework were reported beyond the 2022 local law enactment and the 2024 surcharge addition.
Market Comparison
Chestertown’s April 2026 occupancy of 24.85% is well below the US STR median of approximately 55%, but April is the market’s off-season shoulder period. The 2025 full-year average of 43.9% is more representative and still below the national median, reflecting the concentrated seasonality of a dual-peak mountain market. The $234.81 April ADR is above the US STR median of approximately $220, and the 2025 full-year average ADR of $314 is substantially above the national median, confirming strong pricing power in peak periods.
The professional management landscape is led by operators with strong ratings. Evolve leads with 166 listings and 6,967 reviews (4.77 average rating). Adirondack By Owner follows with 97 listings and 3,146 reviews (4.83 rating). Vacasa holds 73 listings with 2,151 reviews (4.58 rating). Northern Living manages 66 listings with 2,312 reviews and the highest rating in the top five at 4.85. Rocky Point Properties rounds out the top five with 57 listings and 530 reviews (4.82 rating). The top five collectively manage 459 listings, approximately 7.5% of the 6,137 total listing records, indicating a fragmented, predominantly independent host market with several regionally focused specialty operators earning strong guest satisfaction scores.
Frequently Asked Questions About Chestertown, New York
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