Windham Is Open, Hunter Has a Cap: What That Means for a 2026 Catskills Rental Purchase

Thomas Garner
Jul 28
12 min read

Updated: Aug 7

If you're an NYC-area buyer working a shortlist of Catskills properties right now, you've probably noticed that Windham and Hunter get marketed almost interchangeably — same ski corridor, same Route 23A drive time, same "mountain house" listing photos. They are not the same regulatory bet, and the difference matters more to your 2026 purchase math than square footage or granite countertops.

Windham has no short-term rental permit, no fee, and no cap. Hunter, despite sitting one exit down the same mountain, operates under a 2023 local law that requires a permit, a compliance bond, a fire-safety inspection, and — critically — caps the total number of active STR permits townwide. Two towns, two very different entry conditions, and if you're deciding where to put money down this year, you need to understand both before you fall for a listing photo.

Windham: Still an Open Door, With a Recent History Worth Knowing

Windham's current rule is simple because there isn't much of one. As of 2026, the town does not require a short-term rental-specific permit or license to operate. There's no cap on the number of STRs, no per-unit fee, and no annual renewal paperwork tied to hosting. Owners still have to comply with ordinary things — zoning district use, noise and nuisance rules, and proper collection and remittance of applicable occupancy taxes — but there's no gatekeeping mechanism standing between a closing and a live listing.

That openness isn't accidental, and it isn't guaranteed to last forever. Back in 2020, Windham's Town Board floated one of the stricter draft STR laws discussed anywhere in the Catskills at the time — a proposed cap of just 150 total permits across Windham, Hensonville, and Maplecrest, plus rental-day limits. A petition drew more than 1,400 signatures in opposition, and the board withdrew the draft that November. Windham has operated permit-free since, but the fact that a cap was seriously on the table once is a reasonable data point for any buyer modeling a multi-year hold: open-entry towns here aren't immune to regulatory reversal, and nothing guarantees today's rules hold in year three or four of ownership.

For a 2026 buyer, the practical read is this: Windham remains the easiest on-ramp of the two towns, but "easy" should be read as "currently easy," not "permanently exempt." Build in at least a mental placeholder for a future board revisiting the question, especially as growing rental density starts drawing the same neighbor complaints that pushed the 2020 draft in the first place.

Hunter: The Same Corridor, a Genuinely Different Rulebook

Hunter is marketed alongside Windham constantly — same mountain, same drive-up base village energy, same target renter. But Hunter passed Local Law No. 2 of 2023, and it is a real regulatory system, not a formality. The requirements as adopted:

A permit is mandatory before any short-term rental can legally operate in the Town of Hunter.
Initial permit fee of $500, with a $250 renewal fee on subsequent cycles.
A $1,000 compliance bond held against the property/operator.
A mandatory fire-safety inspection before a permit is issued.
A townwide cap of 250 total STR permits — a hard ceiling on how many legally operating short-term rentals Hunter will allow at any one time.
Permits are non-transferable to a new owner on resale, which means a buyer cannot simply assume the previous owner's operating rights convey with the deed.

That combination — fee, bond, inspection, and especially the numeric cap — puts Hunter in a fundamentally different category from Windham, even though the two cast very similar shadows in a Zillow search radius or a real estate agent's regional description.

Is the 250-Permit Cap Actually Binding Right Now?

Here's where a buyer needs to slow down and separate "there's a cap" from "the cap is currently limiting new entrants." Those are two different questions, and conflating them is an easy way to either overpay for false scarcity or walk away from a town that still has room.

Public data on active Hunter listings is genuinely inconsistent depending on how the market boundary is drawn. One major short-term rental data aggregator lists roughly 453 active vacation rental listings mapped to the "Hunter, NY" market — a boundary that almost certainly bleeds into neighboring hamlets and unincorporated areas well beyond the Town of Hunter's actual jurisdiction. Other sources, scoped more narrowly, put the number of STRs actually operating inside town lines closer to the double digits to low hundreds. That's a wide enough spread — anywhere from roughly 55 to 453 depending on whose map you trust — that no outside data source can currently tell you with confidence how close Hunter is to its 250-permit ceiling.

The honest takeaway: whether the cap is currently binding as an outright barrier to new permits is unconfirmed from public sources — nobody outside the Town of Hunter's own permit ledger actually knows the real number holding a valid, current permit today. Given how directly this affects a purchase decision, the only reliable move is to call the source directly:

Town of Hunter Building Inspector: (518) 589-6150

Before signing anything on a Hunter property with the intent to operate it as a short-term rental, confirm three things with that office: how many of the 250 permits are currently issued and active, whether the seller's existing permit (if any) is being surrendered or lapses at closing, and current processing time for a new application. Because permits are non-transferable, a Hunter purchase almost always means applying for a brand-new permit as the incoming owner — not inheriting one — so knowing the live count against the cap, not the marketing pitch, should drive your timeline and your offer.

What a New Owner Is Actually Walking Into: Competition, Not Scarcity

Whichever town you land in, be honest with yourself about the current market condition: a 2026 buyer in the still-open corridor is walking into a crowded field, not an empty one. Renovated A-frames — the once-novel Catskills signature — are now a commodity look. Search any of these markets and you'll find dozens of nearly identical listings: cedar-clad A-frame, black-and-white kitchen, wood stove, hot tub on the deck, moody interior photography. The property type that used to differentiate a listing on its own now blends into the background.

At the same time, the top of the market has moved. AvantStay's Catskill-area flagship, the River House — an 11-bedroom riverfront estate — books at roughly $1,000 a night, and it's become something of a reference point for how far the ceiling has risen on large-format, professionally managed Catskills properties. That's not the segment most individual buyers are competing in, but it recalibrates guest expectations across the whole region: renters increasingly expect resort-caliber styling, amenities, and photography even from a modest three-bedroom cabin, because that's the visual bar the market's most visible listings have set.

Supply growth in the broader Catskill-area market has also been dramatic. Data for the Catskill village submarket specifically shows year-over-year listing supply increasing by well over 1,000% in some recent read-outs — a market "recalibrating around a new competitive baseline," in the words of one industry tracker. Whatever the exact percentage, the direction is unambiguous: more operators, more listings, more competition for the same finite pool of weekend and ski-season demand.

The real pivot for a 2026 buyer, then, isn't finding a property nobody else has thought of. That property mostly doesn't exist anymore in Windham or Hunter. The differentiator is how well a given property gets marketed and positioned against a flood of near-identical inventory — direct-booking presence, photography and styling that doesn't just meet the A-frame template, pricing strategy tuned to shoulder seasons rather than just peak ski and fall-foliage weekends, and a brand story that gives a guest a reason to pick this cabin over the twenty other cabins that look just like it in a search grid.

The Honest Revenue Picture: Ranges, Not a Single Number

Anyone showing you a single projected revenue number for a Catskills STR purchase in 2026 is oversimplifying. Directional, AirROI/AirDNA-style estimates for this cluster vary meaningfully by data source, time window, and how tightly the market boundary is drawn — but the broad strokes are consistent enough to be useful for underwriting, as long as you treat them as ranges:

Hunter carries a meaningful share of the cluster's premium inventory. Estimates put average annual revenue per listing in the neighborhood of the mid-$30,000s to mid-$50,000s, occupancy in roughly the low-to-mid 30s to mid-30s percent, and average daily rates running well above the regional median — reflecting Hunter Mountain's ski-season pull and a supply mix that skews toward larger, higher-end homes.
Windham should be modeled in a similar band directionally, though publicly available aggregator data specific to the town is thinner and easily confused with same-named markets elsewhere in the country — a reminder to verify any third-party number against the specific New York, Greene County listing set before you rely on it.
Catskill village — the walkable riverside village, not the towns of Hunter or Windham — is the smallest and weakest piece of this cluster by the numbers. Depending on the data source, average annual revenue there runs meaningfully lower than the ski-corridor towns, occupancy estimates cluster in roughly the low-to-mid 30s percent (with at least one source reading closer to the mid-40s, underscoring how much these figures shift by methodology), and the active listing count is small enough that a handful of professionally managed entrants can visibly move the market's averages. Don't lean on Catskill village performance alone as your investment case — it's a complement to a ski-corridor property, not a substitute for one.

Treat every one of these figures as a planning range, not a promise. Verify current numbers against a live aggregator pull before you finalize an offer, and stress-test your underwriting at the low end of each range, not the midpoint.

Woodstock and Kingston Are a Different Conversation Entirely

It's worth being precise here: Woodstock and Kingston sit in a separate cluster from the Hunter/Windham/Catskill ski corridor, and the honest answer for a buyer targeting either town is categorically different from anything above.

Woodstock caps its program at 55 owner-occupied and 55 non-owner-occupied STR registrations — all currently allocated, with the town maintaining a waiting list for openings that occur only when an existing operator doesn't renew. Non-owner-occupied rentals are further limited to 180 days a year. There is no meaningful "buy a house and start hosting" path in Woodstock in 2026.

Kingston has reached its permit cap as well. In practice, that leaves a new buyer with exactly two routes into legal STR operation there: buy a property that already holds a valid, transferable permit (rare, and priced accordingly by sellers who know what they're holding), or occupy the property as a genuine primary residence and operate under Kingston's owner-occupied allowances.

If a listing agent tells you Woodstock or Kingston are "just like Hunter, just get a permit," that's not accurate as of 2026 — both are effectively closed programs unless you're buying an existing, transferable permit or committing to live there yourself.

The New Statewide Layer: Registry Verification Before Any Listing Goes Live

Layered on top of all local rules, New York State's short-term rental registry law — S.885C/A.4130C, signed December 2024, with the implementation framework finalized by a Chapter 99 of the Laws of 2025 amendment (S.820/A.5686, signed February 2025) — authorizes counties to stand up short-term rental registries and requires booking platforms to verify a host's county registry number before a listing can go live. This is a statewide mechanism sitting above whatever Windham, Hunter, Woodstock, or Kingston individually require — it doesn't replace local permitting, it adds a registry-verification checkpoint that platforms are expected to enforce.

Greene County — home to Windham, Hunter, and Catskill — has stood up its own registry portal. As of now, registering is free and, per the county's own guidance, not mandatory in the way a local town permit is, but a 2026 buyer should treat "verify my registry status before listing day" as a standard pre-launch step rather than an afterthought, since platform-side verification requirements are still being implemented and could tighten. Questions can go to Greene County's tourism office.

The Bottom Line for a 2026 Buyer

Windham still offers the closest thing to unrestricted entry in this corridor, but its own 2020 near-miss with a strict cap is a fair warning that "no rules today" isn't the same as "no rules ever." Hunter is a genuinely regulated market — permit, bond, inspection, and a 250-unit cap — but the honest, unresolved question is whether that cap is currently binding, and the only way to know is a direct call to the Town of Hunter Building Inspector before you write an offer. Either way, you're buying into a crowded, well-photographed submarket where the property itself is no longer the differentiator — professional-grade marketing and positioning against a flood of look-alike A-frames is. And if your search wanders toward Woodstock or Kingston, recognize immediately that you're in a different cluster with a different, much narrower rulebook: permit-cap towns where a transferable permit or genuine primary residency is the only route in.

Work with Crest & Cove Creative

Buying into a capped or crowded Catskills market means your listing has to out-market the competition, not just out-renovate it. Whether you're closing on an open-entry Windham property or navigating Hunter's permit math, Crest & Cove Creative builds direct-booking brands and listing positioning for independent STR operators in emerging corridors like the Catskills. Get a free look at your market position at crestcove.co, email info@crestcove.co, or call (256) 998-7502.

Frequently Asked Questions

Is the Catskills a good investment in 2026? It depends heavily on which town and which permit environment you're buying into. Windham and Hunter still see meaningful ski-season demand and command some of the region's highest average daily rates, but supply has grown sharply across the cluster, meaning new owners are entering a competitive, well-supplied market rather than a scarce one. Underwrite using conservative, range-based revenue assumptions rather than a single optimistic number, and factor in that differentiated marketing — not the property alone — is what separates a strong performer from an average one.

What is Hunter NY's STR permit cap? Hunter's Local Law No. 2 of 2023 caps total short-term rental permits townwide at 250. The law also requires a $500 initial permit fee ($250 on renewal), a $1,000 compliance bond, and a mandatory fire-safety inspection. Permits are non-transferable, so a buyer cannot simply take over a seller's existing permit at closing.

Does Windham NY require a short-term rental permit? No. As of 2026, Windham has no STR-specific permit, license, fee, or cap. Owners still need to follow standard zoning, noise, and tax-remittance rules, but there is no permitting gate to clear before listing a property. A stricter draft law with a 150-permit cap was proposed in 2020 and withdrawn after public pushback, which is worth keeping in mind for long-term planning.

Is there a Kingston NY STR permit waitlist? Kingston's short-term rental permit cap has been reached, and the city does not currently maintain an open, "apply and wait" queue in the way some capped towns do. In practice, new entry is largely limited to purchasing a property with an existing, valid, transferable permit or operating under Kingston's owner-occupied allowances as a genuine primary residence.

How do I confirm current STR rules before buying a property in Hunter or Windham? For Hunter, call the Town of Hunter Building Inspector's office directly at (518) 589-6150 to confirm the current number of active permits against the 250-unit cap, whether a seller's permit lapses at closing, and current application processing times. For Windham, confirm zoning district eligibility and current town code directly with the town, since rules that don't require a permit today can still change with a future board vote. Both towns also fall under Greene County's short-term rental registry and New York State's statewide registry-verification requirement under Chapter 99 of the Laws of 2025.

What's driving Catskills short-term rental competition beyond regulation? Supply growth. Renovated A-frame cabins, once a differentiator, are now a common look across Windham, Hunter, and the surrounding villages, and professionally managed operators — including large-format properties commanding roughly $1,000 a night — have pushed guest expectations for styling and amenities higher across the board. A 2026 buyer is competing on marketing, pricing strategy, and direct-booking presence more than on the property type itself.

About the Authors

Crest & Cove Creative is a short-term rental marketing agency founded by Thomas Garner and Jacob Mishalanie. We build direct-booking brands, listing optimization systems, and market-specific content strategies for independent STR operators nationwide, including emerging corridors like New York.