Windham, New York Short-Term Rental Market
Windham, NY STRs averaged $263/night at 43.0% occupancy in April 2026, with no permit required and revenue up 2.9% year-over-year.
Quick Answer: Windham, New York is an active short-term rental market. average occupancy is 51%. average monthly revenue is $4,487. average daily rate is $335. the top operator 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 Apivex evaluates per market.
Market Overview
Windham is a Catskill Mountains ski and outdoor recreation destination in Greene County, NY, approximately 2.5 hours from New York City. The market draws roughly 1 million visitors per year, anchored by Windham Mountain Resort’s year-round programming including 54 ski trails, a mountain bike park, and an alpine spa. As of April 2026, the market posted an average daily rate of $263 and occupancy of 43.0%, generating a RevPAR of $113.
The market holds approximately 13,944 active listings, with entire-place rentals at 12,455 (89.3%), private rooms at 1,452 (10.4%), and shared rooms at 37. This is the highest private-room share in this batch, reflecting the market’s mix of vacation homes and year-round residential properties with rooms available for rent. Bedroom distribution shows 1-bedroom units leading with 4,458 listings, followed by 3-bedroom (3,345), 2-bedroom (2,805), 4-bedroom (1,921), and 5-bedroom-plus (1,388). Channel distribution is heavily Airbnb-weighted: 7,684 exclusively on Airbnb, 5,605 on both platforms, and 655 on Vrbo only.
Year-over-year in April 2026: occupancy fell 3.3%, ADR rose 4.8%, and revenue grew 2.9%. Revenue growth in a quarter where occupancy declined indicates successful rate management. The investability score of 85.8 and seasonality score of 77.5 reflect a multi-season mountain market with a healthier demand distribution than summer-only beach destinations.
Seasonal Patterns
| Month | Occupancy | ADR | Revenue |
|---|---|---|---|
| Jan | 38% | $267 | $2,975 |
| Feb | 46% | $273 | $3,093 |
| Mar | 39% | $230 | $2,646 |
| Apr | 48% | $227 | $2,735 |
| May | 51% | $251 | $2,928 |
| Jun | 53% | $277 | $3,667 |
| Jul | 60% | $280 | $4,387 |
| Aug | 62% | $288 | $4,694 |
| Sep | 48% | $256 | $3,295 |
| Oct | 52% | $269 | $3,852 |
| Nov | 44% | $256 | $3,152 |
| Dec | 46% | $270 | $3,272 |
Top Short-Term Rental Operators in Windham
Ranked by total active listings. Useful for understanding the competitive landscape.
| # | 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 pricing by property type, tier, and bedroom count.
Revenue by Bedroom Count
| 1 bed | 4,458 |
| 2 bed | 2,805 |
| 3 bed | 3,345 |
| 4 bed | 1,921 |
| 5 bed | 1,388 |
ADR by Property Tier
| Entire Home | $363 |
| Luxury | $683 |
| Professionally Managed | $556 |
Revenue by Dwelling Type
| Apartment | $2,995 |
| Entire Place | $4,805 |
| House | $4,938 |
Booking Channel Mix
Distribution of bookings across major STR platforms.
| Channel | Share |
|---|---|
| airbnb | 55.1% |
| vrbo | 4.7% |
| both | 40.2% |
Investment Analysis
Windham presents a NYC-proximity mountain market with no STR permit requirements and solid revenue fundamentals. The typical home value is not published in available data sources. The median list price is $660,817 with 61 active for-sale listings. Using the median list price as the entry cost proxy, at the average monthly revenue of $3,012, annualized gross revenue projects to approximately $36,144, implying a gross yield of roughly 5.5% against median list price.
Tier differentiation is pronounced: luxury-tier properties average $529/night versus the all-listings ADR of $263, more than double. Professionally managed listings average $397/night, a 51% premium over market. This PM premium is among the highest in this batch, suggesting that PM operators in Windham control significantly higher-rate inventory. House listings and entire-place listings average similarly at $3,260 and $3,223 per month respectively.
The investability score of 85.8 is one of the stronger readings in this batch. The March 2020 through 2021 COVID-era demand surge (61.82% occupancy in 2020, $228 ADR; 59.06% in 2021, $281 ADR) established a new permanent baseline well above pre-2020 levels. Annual revenue has stabilized in the $3,578 to $3,851 range from 2023 through 2025, suggesting a normalized plateau following the post-pandemic adjustment. The absence of a local STR permit requirement is a material advantage for operators.
Revenue Trend (5 yr)
ADR & Occupancy Trends (5 yr)
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Windham guests book an average of 38.2 days in advance, approximately five to six weeks out. This shorter lead time reflects the NYC drive-market character: guests from New York City and the surrounding metro area tend to book closer to their stay date than destination tourists who require flights. Weekend getaway bookings in particular often occur 3 to 5 weeks in advance.
Average length of stay is 3.6 nights, reflecting the Friday-through-Monday mountain-retreat pattern. The 3 to 4 night LOS is consistent with the area’s positioning as a long-weekend escape from the NYC metro. Operators benefit from relatively low turnover costs versus 2-night markets. A 3-night minimum in winter and summer peaks and a 2-night minimum in shoulder months captures both the extended weekend and the mid-week casual traveler.
Short-Term Rental Regulations
Windham has no town-level STR permit, license, or registration requirement. A draft local law proposed in 2020 that would have capped STR permits at 150 and limited rentals to 100 days per year was formally withdrawn on November 30, 2020 following community pushback. Enforcement today is complaint-based and tied to general code, noise, nuisance, and zoning compliance.
There is no owner-occupancy requirement and no primary-residence requirement. STRs are generally allowed in residential zones throughout Windham subject to standard building and safety codes. Enforcement severity is rated low.
New York State sales tax (4%) plus Greene County local sales tax (4%) applies to STR receipts, for a combined 8% on bookings. Operators should confirm directly with the Greene County Treasurer whether any separate county occupancy tax applies to their parcel, as available documentation is ambiguous for the Town of Windham specifically. Airbnb typically handles NY state and county sales tax collection automatically.
A statewide New York STR registry law enacted in 2024 through 2025 creates new state-level registration and reporting obligations for STR operators across all counties, including Greene County, which has opened a voluntary registration portal. Even hosts in towns without local STR ordinances now face state-level registration requirements as that program rolls out. Operators should register with the state system regardless of local permitting status.
Market Comparison
Windham’s $263 ADR slightly exceeds the U.S. STR median of approximately $220, reflecting the NYC-proximity mountain premium. The 43.0% April occupancy is below the annual U.S. median of approximately 55%, consistent with a spring shoulder month in a ski-and-summer market where demand is strongest at the season endpoints.
Year-over-year revenue grew 2.9% in April 2026, one of the stronger performance readings in this batch. The 2025 full-year average of $3,848/month is at the upper end of the post-2022 normalized range, suggesting the market has stabilized at a new, higher baseline following the 2020 to 2021 COVID-era demand surge.
Among property managers, Evolve leads with 284 listings and 10,524 reviews (4.64 rating). Red Cottage follows with 151 listings and a strong 4.88 rating. Home Sweet Hudson holds 65 listings (4.74 rating). The Upstate Place Team (47 listings, 4.89 rating) and AvantStay (38 listings, 4.57 rating) round out the top five. The combined top-5 count of 585 listings represents roughly 4.2% of the approximately 13,944 total market listings, reflecting the high proportion of self-managed hosts in this market.
Frequently Asked Questions About Windham, New York
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