Windham, New York Short-Term Rental Market
Windham has no town STR permit; Catskills and Hudson Valley August ADR $371, occupancy 59.1%, revenue $6,049.
Quick Answer: Windham, New York is an active short-term rental market. average occupancy in the Lower Hudson Valley market area is 47%. average monthly revenue in the Lower Hudson Valley market area is $4,139. average daily rate in the Lower Hudson Valley market area is $317. the top operator in the Lower Hudson Valley market area is Evolve with 284 listings. market score is 75/100 (grade B).
Market data reflects the Lower Hudson Valley regional market, which includes Windham. Regulations, taxes, and permit details below are specific to Windham.
Market Score Breakdown
Five dimensions StaySTRA evaluates per market.
Market Overview
Apivex reports Windham performance data as part of a shared Catskills and Hudson Valley series. The same figures appear for 13 other towns, including Margaretville, Fleischmanns, Arkville, Monticello, Hudson, Kinderhook, and Newburgh. All performance numbers on this page therefore describe the Catskills and Hudson Valley STR market, not Windham alone. In August 2026, the newest month in the data, that market posted an average daily rate (ADR) of $371, occupancy of 59.1%, and average revenue of $6,049 per listing for the month.
Year over year, ADR rose 7.9%, occupancy fell 4.9%, and revenue rose 3.9%. Across 2025, the annual averages were an ADR of $296, occupancy of 47.1%, and monthly revenue of $3,847. The first eight months of 2026 average an ADR of $315, occupancy of 47.3%, and monthly revenue of $4,070, so 2026 is running ahead of 2025 mainly on rate.
Windham itself is a small mountain town of 1,708 residents. The area profile reports roughly 1 million visitors a year, mostly skiers and snowboarders in winter and hikers and mountain bikers in summer. Visitors skew toward the New York City metro area, within about 2.5 hours by car, and the typical stay is 3 to 4 days. Windham Mountain Resort is the main draw, with 54 trails across 285 skiable acres and a year-round mountain bike park. The Mountain Top Arboretum in nearby Tannersville and the 1.7-mile Windham Path add summer and shoulder-season reasons to visit. Listing counts, listing-type mix, and bedroom mix are tracked at a shared regional level rather than uniquely for Windham, so this profile omits them.
Seasonal Patterns
| Month | Occupancy |
|---|---|
| Jan | 38% |
| Feb | 46% |
| Mar | 39% |
| Apr | 48% |
| May | 51% |
| Jun | 53% |
| Jul | 60% |
| Aug | 61% |
| Sep | 48% |
| Oct | 52% |
| Nov | 44% |
| Dec | 46% |
Month-by-month nightly rates and revenue figures for Windham are available to StaySTRA Pro members. Unlock with StaySTRA Pro or analyze a specific address free.
Top Short-Term Rental Operators in Lower Hudson Valley market area
Ranked by total active listings. Useful for understanding the competitive landscape. Operator data is published for the Lower Hudson Valley market as a whole, which includes Windham, so these counts are not Windham-only figures.
| # | Operator | Listings | Reviews | Rating |
|---|---|---|---|---|
| 1 | Evolve | 284 | 10,524 | ★ 4.64 |
| 2 | Red Cottage | 151 | 3,895 | ★ 4.88 |
| 3 | Home Sweet Hudson | 65 | 3,085 | ★ 4.74 |
| 4 | The Upstate Place Team | 47 | 2,096 | ★ 4.89 |
| 5 | AvantStay | 38 | 901 | ★ 4.57 |
What Kind of STR Should I Buy in Windham?
Revenue and nightly-rate breakdowns by bedroom count, property tier, and dwelling type for Windham 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 | 55.1% |
| vrbo | 4.7% |
| both | 40.2% |
Booking Insights
Booking-window and length-of-stay analysis for Windham — 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
Windham has no town-specific short-term rental permit, license, or registration requirement. Zoning has no STR overlay, and STRs are generally allowed in residential zones, including single-dwelling and multi-dwelling districts, subject to standard building, safety, and nuisance codes. Enforcement is rated low and is complaint-based, tied to general code, noise, nuisance, and zoning rules.
A 2020 draft local law would have capped STR permits at 150 across Windham, Hensonville, and Maplecrest and limited rentals to 100 days per year. Town Supervisor Thomas Hoyt withdrew it on November 30, 2020, after a petition with more than 1,400 signatures. Town Board members have indicated they may revisit STR rules in the future, so the rules could change.
Hosts owe New York State sales tax of 4 percent plus 4 percent Greene County sales tax, for a combined 8 percent on STR receipts. A county-wide occupancy tax is not clearly documented for Windham, so confirm with the Greene County Treasurer. A 2024 to 2025 New York law creates a state-level STR registry, and Greene County has opened a voluntary registration portal. Hosts in towns without local STR laws now face state registration and reporting duties as the program rolls out.
Market Comparison
The Catskills and Hudson Valley STR market posted 59.1% occupancy in August 2026, above the rough US STR median of about 55%. Its ADR of $371 is about 69% above the US median of roughly $220. This is a high-rate market, driven by luxury and professionally managed listings at $720 and $573.
The 2025 annual averages tell a different story. Occupancy was 47.1% and ADR was $296, so the market runs below the national occupancy median across the full year, and the summer months lift the picture. August year over year shows rates up 7.9% and occupancy down 4.9%.
Top-operator rankings are tracked at a shared regional level rather than uniquely for Windham, so this profile omits them. Windham-specific results can differ from the regional average. The Windham facts to weigh are a ski-led visitor base, no local STR permit, and a median list price of $603,117. Compared with national medians, this is a high-rate, seasonal market.
Frequently Asked Questions About Windham, New York
Are short-term rentals legal in Windham, NY?
What taxes apply to STRs in Windham?
How much do STRs earn in the Catskills and Hudson Valley region that includes Windham?
What is the best month for STRs in this region?
How far ahead do guests book?
What does a home cost in Windham?
Analyze Windham Rentals
Use our free calculator to estimate Airbnb revenue for any property in Windham.
Free Windham STR Calculator →
