Woodstock Short-Term Rental Regulations: A 2026 Guide For Airbnb Hosts

Do you own a place in Woodstock and you're weighing whether to put it on Airbnb or Vrbo? Well, the good news is that the town allows short-term rentals outright, and it's been that way since May 2019. The catch is the cap. Woodstock's Town Board decides each year how many STR permits may exist at all, and that ceiling has spent most of the last few years full, with a waiting list sitting behind it.

Which Woodstock, though? This one is the Town of Woodstock in Ulster County, New York, up in the Catskills, and not the Village of Woodstock in Vermont, whose ordinance is completely different and which search results mix up with this one constantly. It isn't New York City either, so none of the Local Law 18 machinery applies here. What governs is Chapter 260, the town's zoning law, and it sorts every rental into one of three named categories that get treated very differently.

So let's walk through what it actually takes to do this properly: which category your place falls into, what a permit costs and how long the queue is, the documents the Building Department wants to see, the two layers of tax stacked on top of your nightly rate, how hard any of it gets enforced, and who to call when you get stuck. One housekeeping note first. Woodstock's own website was offline every time I tried it in July 2026, so where I link a town page below it points at the Internet Archive's copy rather than at a dead address. And if you're weighing a Woodstock house against a market with no permit queue at all, run both through BNBCalc first.

What are Short-Term Rental (Airbnb, VRBO) Regulations in Woodstock, New York?

Before you can model anything, though, you need to know which of the three categories your property falls into, because Woodstock's whole system hangs off that one choice.

Two documents do most of the work. Local Law No. 1 of 2019 amended Chapter 260 "to permit and regulate bed and breakfasts and short-term rentals," and it now lives at § 260-56 of the zoning law with the definitions at § 260-123. Alongside it, the Schedule of Use Regulations decides which districts each category is allowed in, and its amendment history dates the STR rows to May 21, 2019.

A short-term rental in Woodstock means a stay of less than thirty days in at least one room of a private home or a habitable accessory structure. From there the law splits three ways:

Category	What it covers	Owner on site?	Maximum lodgers	Zoning
STR home	1 to 2 bedrooms let inside the residence	Yes, the owner must live on the property	4	Permitted in every district except the Floodway
STR establishment	3 to 5 bedrooms let inside the residence	Yes, the owner must live on the property	10	Special use permit in R8, R5, R3, R1.5 and HR; permitted in HC, NC and LI/SLI
STR non-owner-occupied	The entire residence, no host present	No, but a local Host is required	2 per bedroom	Special use permit in every district, prohibited in the Floodway

That last row is where most investors land, and it carries three restrictions the other two don't.

A non-owner-occupied STR may be rented for no more than 180 days per calendar year, and no more than 26 of those may be weekends or parts of weekends. A weekend, for this purpose, is any time between Friday evening and Monday morning. It also needs a designated Host, which the law defines as an adult living within ten miles of the property who can deal with emergencies and guest problems within 24 hours.

And only the property owner may register. An individual can register or hold an interest in exactly one non-owner-occupied STR, while registration by a corporation whose owners hold interests in more than one STR is prohibited outright in residential districts.

Some rules apply whatever category you're in. Occupancy is capped at two guests per bedroom, and the maximum for the house has to be posted inside it, though children aged twelve and under aren't counted as guests. Parking runs at one space per bedroom on top of whatever the principal residence already needs.

You'll also have to post a safety and egress plan in a visible spot and on the back of every bedroom door, hand guests the local noise, fire and safety rules along with emergency contacts and a map showing the property boundaries, and keep garbage receptacles out for no more than 24 hours at a stretch.

One rule catches people who are used to other markets. Woodstock assigns each approved rental a registration number, and that number has to appear in every listing you run, print or online. On-site advertising, meaning a sign at the house, is banned.

Starting a Short-Term Rental Business in Woodstock

Registration numbers and egress plans are the easy part, honestly. The hard part is getting a permit to exist at all, and unfortunately for anyone reading this as an investment plan, the category you probably want is the one Woodstock has squeezed hardest.

Under § 260-56 F, the Town Board sets the caps on the number of owner-occupied and non-owner-occupied STRs permitted in town, plus the fee schedule, on an annual basis. That single sentence is the whole business model. There's a finite number of permits, the Board can move the number in either direction each year, and when it's full you go on a waiting list until somebody stops renewing.

I couldn't confirm the 2026 caps from the town's own pages, since its website was down throughout my research, so treat the reported history as direction rather than gospel. Hudson Valley One put the split at 280 owner-occupied and 75 non-owner-occupied permits in September 2022, with only fifteen owner-occupied slots free at the time. The following April it reported a cap of 340 that had been cut to 285.

You can see why the town got protective. Ulster County's own tracking put Woodstock at 383 short-term rentals against 4,250 housing units, or 7%, in its 2022 to 2023 snapshot.

The Ulster County Comptroller's Short-Term Rental Report 2025, released that September, still had Woodstock in the top four towns countywide with over 7% of its housing stock operating as short-term rentals. The county average was 3.28%, and the Housing Smart Communities recommendation is 2%. When the county's own auditor is writing that STRs "are shifting homes from residents to tourists," a town board is not about to raise the ceiling.

So what's actually available? Assuming your plan can survive it, the owner-occupied route is the one with room in it. You live in the house, you let one or two bedrooms as an STR home, and you avoid the special use permit, the 180-day ceiling and the weekend count entirely. That's a spare-bedroom business rather than a whole-house one, mind you, and the revenue you should be modeling is a room rate rather than an entire-home rate.

The other honest option is to step outside the regime. A stay of thirty days or longer isn't a short-term rental under § 260-123 at all, so it needs no STR permit and falls under ordinary landlord and tenant law instead. Woodstock has real demand for furnished mid-term stays, and plenty of Catskills inventory has drifted that way. Just make sure you count the nights properly before you assume you've cleared the line, because twenty-nine nights is a short-term rental and thirty isn't.

Short-Term Rental Licensing Requirement in Woodstock

Assuming a permit is genuinely available to you, the process itself still runs through two different town bodies, and it's worth knowing which one owns which piece before you start.

The permit itself is an annual operating permit from the Building Department, and the town's own Building Department page is explicit that bed-and-breakfast establishments, STR establishments, bed-and-breakfast homes, STR homes and STR non-owner-occupied establishments all require one. It runs for a single calendar year, so renewal comes around every year rather than being something you can forget about for a while.

Fees are the piece I could pin down least well, because the town's live fee schedule sits behind a website that wouldn't load in July 2026. What I can source is the town's own Application for Short Term Rental Permit, revised 1/25/2024. It sets a $50 application filing fee due with the application, and an operating fee of $400 plus $50 per bedroom due on approval and annually after that. The form is clear that you don't send the annual fee in with the application.

Since then the Board restructured the schedule. Hudson Valley One reported that a 3-2 vote in January 2025 adopted tiered annual fees instead:

• $250 plus $25 per extra room, for an owner-occupied rental inside the home.
• $350 plus $25 per extra room, where the owner lives on site but lets a separate structure such as a cottage or a space above a garage.
• $450 plus $50 per extra room, for a non-owner-occupied STR.

That's a newspaper's reporting rather than the town's own schedule, though. So as of July 2026, do check the current figure with the Building Department before you write the check, because the fees are designed to move every year.

Then there's the second body. Because the use table requires a special use permit for a non-owner-occupied STR in every district, and for an STR establishment in the residential and hamlet districts, those applications also go to the Planning Board, and the town keeps a separate Short Term Rental SUP application for exactly that. An owner-occupied STR home skips this step, which is a real difference in both time and cost.

Every STR also has to pass a yearly fire and safety inspection, and the inspection report gets attached to the annual renewal application. All units must meet New York State Building Code requirements, and the permit application has you sign an acknowledgement that the property is subject to inspection by the town. Remember that this is annual, not one-time: a permit you can't get inspected is a permit you can't renew.

A few smaller mechanics decide more than they look like they should. Registrations are transferable, but only with a new application, and the transfer has to be applied for within 30 days of a sale. A buyer who sits on that paperwork can lose the permit that made the house worth buying.

Failure to comply with the standards results in denial. And three or more violations of local laws may lead to revocation of an approved operating permit, which in a capped market means the slot goes to somebody on the waiting list rather than back to you.

Required Documents for Woodstock Short-Term Rentals

Since a denial in a capped town costs you a queue position rather than just a fee, it pays to send a complete file the first time. The permit application lists what has to travel with it, and the checklist is short but unforgiving:

• Proof of residence. This is how the town tests owner-occupancy for the STR home and STR establishment categories.
• A copy of the tax map with your property highlighted.
• A safety and egress plan, which also gets posted inside the unit and on the back of each bedroom door.
• A layout of the property, or site plan.
• A parking plan, showing one space per bedroom plus the spaces the principal residence already requires under § 260-30.
• A garbage removal plan. Receptacles can't be left out for more than 24 hours.
• A potable water test, if the property is on a private well rather than public water.
• A copy of your Ulster County Certificate of Authority. The town won't process an STR application without proof you've registered with the county to collect occupancy tax.
• A notarized affidavit and affirmation of the local law.

Non-owner-occupied applicants add one more: the name and contact information of the designated Host, which goes to the Building Department and gets posted inside the rental. When that contact changes you have to notify the Building Department and revise the posted renter notices, so don't forget to update it if you switch property managers mid-season.

Two details from the form are worth heading off early. The office-use block records "Open Permits or Violations," so an unresolved building permit on your property is a live problem before you even reach the STR question. And if you're filing as an LLC, the form asks for a list of owners or your corporation papers, which is how the town enforces the one-STR-per-interest rule against corporate applicants in residential districts.

Woodstock Short-Term Rental Taxes

Assuming you get through all of that and are able to start hosting, there's still tax to deal with, and it comes from two governments rather than from the town. Woodstock itself levies no lodging tax that appears anywhere on its own pages. Ulster County and New York State do the collecting here.

Charge	Rate	Collected by
New York State sales tax	4%	Booking service registered as a NYS sales tax vendor, otherwise you
Ulster County local sales tax	4%	Same, remitted to the NYS Department of Taxation and Finance
Ulster County hotel, motel and STR occupancy tax	4%	Airbnb and Vrbo remit it to the county; you still file the return
Town of Woodstock lodging tax	None	Not applicable

Sales tax first, since it's the layer that changed most recently. New York extended sales tax to short-term rental unit occupancy effective March 1, 2025 wherever the rate exceeds $2.00 per unit per day, and it made booking services register as sales tax vendors and collect on the occupancies they facilitate. The combined state and local rate in Ulster County is 8%, reporting code 5111, per Publication 718. Guests who settle in for 90 consecutive days or more count as permanent residents and fall out of the tax entirely.

The county piece is separate, older, and the one hosts get wrong. Ulster County's Department of Finance charges a 4% occupancy tax on hotels, motels and short-term rentals, and it has to be stated and charged separately from the rent rather than folded into your nightly rate.

Before you take a booking you need a Certificate of Authority, applied for within three days of commencing business and displayed where guests can see it. Records of every occupancy stay available for inspection for three years. Returns are quarterly, due March 20, June 20, September 20 and December 20.

Airbnb and Vrbo now collect the county occupancy tax and remit it directly, yet the county is unambiguous that you still have to file the quarterly return even when the platform collected everything and you owe nothing. Keep in mind that a nil return is still a return. Failing to file one, or failing to obtain the certificate at all, is a misdemeanor punishable by a fine of up to $1,000 and up to a year's imprisonment, and late payments accrue a 5% monthly penalty plus 1% monthly interest.

That 4% is also newer than a lot of published guidance suggests. The county ran a 2% rate from 1991 until Local Law No. 1 of 2024 doubled it, effective February 1, 2024, and receipts jumped from $3.8 million in 2023 to $8.3 million in 2024 as a result.

The same Comptroller's audit found nine establishments that had stopped filing altogether, plus $251,756 in underpaid tax, penalties and interest, which tells you the county is looking now in a way it wasn't before. Add it all up and a Woodstock guest pays 12% on top of your rate: 8% in sales tax and 4% to the county.

New York Wide Short-Term Rental Rules

Those two tax layers are state and county creations, and the same is true of the framework sitting above Woodstock's zoning law, which changed more between 2024 and 2026 than the town's own rules did.

Start with what New York does not do. It doesn't broadly preempt local short-term rental regulation. A New York Department of State training presentation for local governments from April 2025 puts it plainly: it is "up to each municipality to define, prohibit and/or regulate short term rentals as they choose." Woodstock's cap, its weekend count and its one-per-owner rule are all lawful because of that.

Our New York statewide guide walks the whole picture, and the regional contrast is stark, so the Westchester County guide and the Erie County guide are the useful next reads if you're weighing the Catskills against the commuter belt or Buffalo.

What the state did build is a registry. Chapter 672 of the Laws of 2024, signed December 21, 2024, created the statewide short-term rental framework. Then Chapter 99 of the Laws of 2025, signed February 28, 2025, restructured it into a county-run system with a local opt-out and confirmed the March 1, 2025 start for booking-service tax collection.

Counties had until the later of December 31, 2025 or nine months after the registry provisions took effect, which worked out to late June 2026, to pass a local law opting out. That window has closed. Whether Ulster County opted in or out is something I couldn't confirm on any official county page, and its occupancy tax page makes no mention of a state registry, so treat the county's status as genuinely unsettled rather than assuming either way.

The distinction matters, because a county registry brings obligations with it. The New York State Association of Counties implementation memo summarizes them: two-year registrations, an evacuation diagram, posted emergency numbers for police, fire and poison control, a working fire extinguisher, and insurance covering the value of the dwelling plus at least $300,000 for property damage and bodily injury.

A booking service's own coverage can satisfy that insurance requirement. Hosts keep two years of records. Penalties run to $200 for a host's third violation after warnings, and $500 per day per violation for a booking service. None of it binds anyone until the county actually stands a registry up, and towns and villages already running their own systems keep them.

One statewide rule you can mostly set aside here. Multiple Dwelling Law § 4(8)(a) restricts "class A" multiple dwellings to permanent residence purposes, meaning thirty consecutive days or more, and it's the foundation of New York City's near-total ban. Class A classification is overwhelmingly an apartment-building concept concentrated downstate, so a Woodstock single-family house or cottage isn't caught by it. Be aware of it only if you own something in a multi-unit building.

Does Woodstock Strictly Enforce STR Rules?

Yes, although the mechanism looks nothing like the fine-and-inspection model most towns run, and comparing it to one will mislead you.

Woodstock enforces through scarcity. Because the number of permits is finite and has been full, an unpermitted operator isn't competing with a fine, they're competing with a waiting list of neighbors who followed the process. Add the requirement that the town-issued registration number appear in every online listing, and an unregistered Woodstock rental is easy to spot from a laptop.

The revocation trigger cuts the same way. Three or more violations of local laws can cost a permitted host the operating permit, which in a capped town means handing the slot to somebody on the list.

The town also can't rely on headcount. Its Building Department page shows one person, Francis (Butch) Hoffman, serving as Building Inspector, Code Enforcement Officer, Zoning Enforcement Officer, wetlands and watercourse enforcement, and Fire Inspector. Woodstock also keeps a standing nine-member STR Task Force among its boards and committees, which tells you this stays on the agenda.

The county fills part of the gap. Ulster County contracts with Granicus to scan listing platforms and report advertised rentals back, then shares that data with municipalities that ask for it.

The Comptroller's 2025 report is blunt about the limits, though. The interface "is not user friendly and often has errors in the data, such as town location," the data lacks section, block and lot numbers, and requests from towns "do not come frequently and are not addressed promptly by the County." So detection is decent while follow-through stays thin, which is roughly the pattern across the Catskills.

Tax enforcement is the sharper edge, and it comes from Kingston rather than from Woodstock. The county's occupancy tax penalties are criminal, not just civil, and the Comptroller's August 2025 audit recovered a quarter of a million dollars in back tax, penalties and interest from a sample of filers. Watch out for the quarterly filing obligation in particular, because it's the one that applies even to hosts who owe nothing.

How to Start a Short-Term Rental Business in Woodstock

Given how much of this turns on availability rather than on paperwork, the order below matters, and working through it out of sequence is how people spend money on a plan the cap was never going to allow.

1. Ask the Building Department whether a permit is available in your category, before anything else. Owner-occupied and non-owner-occupied permits are capped separately, and the waiting list is the real gate. This one phone call decides whether steps two through nine are worth making.
2. Work out your category honestly. One or two bedrooms with you living there is an STR home. Three to five bedrooms with you living there is an STR establishment. An entire house with no host present is non-owner-occupied, and that's the constrained one.
3. Check your zoning district against the use table. Nothing is allowed in the Floodway, and a non-owner-occupied STR needs a special use permit everywhere else.
4. Register with Ulster County first. You need the Certificate of Authority in hand, because a copy of it has to travel with the town application.
5. If a special use permit applies, budget for the Planning Board. That's a separate application, a separate timeline and a separate approval from the Building Department's operating permit.
6. Assemble the file. Proof of residence, highlighted tax map, safety and egress plan, site plan, parking plan, garbage plan, water test if you're on a well, county certificate, notarized affidavit, and the Host's details if nobody is living there.
7. File and pay the application fee, then the operating fee on approval. Clear any open building permits or violations first, since the form asks about them.
8. Book the fire and safety inspection, and put the next one in the calendar. The report attaches to your renewal, and the permit runs on a calendar year.
9. Put your registration number in every listing, on every platform. Then post the egress plan, the maximum occupancy and the Host's contact details inside the house, and hand guests the local rules and a property map at check-in.

Before you join a queue for any of that, get honest about the revenue. A capped market with a weekend limit prices very differently from an open one, and the Catskill Mountains market is where to look at what nights in this area actually clear, so you can judge whether 180 days and 26 weekends still adds up to a business.

Who to Contact in Woodstock about Short-Term Rental Regulations and Zoning?

Whichever step you get stuck on, four offices cover almost all of it, and every one of them sits at the same address except the county.

Permits, inspections and enforcement

The Woodstock Building Department issues and renews the annual STR operating permit, runs the fire and safety inspection, and holds the code enforcement role.

• Address: 45 Comeau Drive, Woodstock, NY 12498
• Contact: Francis (Butch) Hoffman, Building Inspector and Code Enforcement Officer
• Phone: (845) 679-2113, ext. 13
• Fax: (845) 679-8743
• Email: [email protected]
• Hours: Monday through Friday, 9:00am to 4:00pm

Special use permits

The Woodstock Planning Office supports the Planning Board, which handles the special use permit a non-owner-occupied STR needs in every district.

• Address: 45 Comeau Drive, Woodstock, NY 12498
• Contact: Melissa Gray, Administrative Assistant
• Phone: (845) 679-2113, ext. 16
• Email: [email protected]
• Hours: Monday through Thursday, 9:00am to 4:00pm, closed 1:00pm to 1:30pm; the office is closed Fridays

Local laws, records and FOIL requests

The Woodstock Town Clerk is the route to Town Board resolutions, which is where the annual cap and fee schedule are actually set.

• Address: 45 Comeau Drive, Woodstock, NY 12498
• Contact: Meghann Reimondo and Michele Sehwerert
• Phone: (845) 679-2113, ext. 14
• Email: [email protected], or [email protected] for records requests
• Hours: Monday through Friday, 9:00am to 4:00pm, closed on national holidays

Occupancy tax

The Ulster County Department of Finance issues the Certificate of Authority and administers the 4% occupancy tax and its quarterly returns.

• Address: 244 Fair Street, PO Box 1800, Kingston, NY 12402
• Phone: (845) 340-4052
• Email: [email protected]
• Main county line: (845) 340-3000

For state sales tax and vendor registration, that's the New York State Department of Taxation and Finance rather than either the town or the county, and its Sales Tax Information Center is on 518-485-2889. One last practical note: the Planning Office's published email uses woodstockny.org while every other department uses woodstockny.gov. That's what the town's own page says, so send to the address listed and copy the Town Clerk if you get no reply.

Frequently Asked Questions

Can you run an Airbnb in Woodstock, New York in 2026?

Yes, with an annual operating permit from the Woodstock Building Department under § 260-56 of the town's zoning law. The town recognizes three categories: an STR home of one to two bedrooms and an STR establishment of three to five, both of which require the owner to live on the property, and a non-owner-occupied STR of the whole house. The Town Board caps the number of permits each year, and the cap has been reached repeatedly, so a waiting list is the normal experience for new applicants.

How many nights a year can you rent a non-owner-occupied short-term rental in Woodstock?

A maximum of 180 days per calendar year, and no more than 26 of those may be weekends or parts of weekends. Woodstock defines a weekend as any time between Friday evening and Monday morning, so a Saturday night booking consumes one of the 26 whether or not the guest stays Sunday. Owner-occupied STR homes and STR establishments have no equivalent night limit. A non-owner-occupied rental also needs a special use permit and a designated Host living within ten miles.

What taxes apply to a Woodstock, New York short-term rental?

Two layers, totalling 12% on top of the nightly rate. New York State and local sales tax comes to 8% in Ulster County, collected by booking services that are registered as New York sales tax vendors since March 1, 2025. Ulster County adds a 4% hotel, motel and short-term rental occupancy tax, which Airbnb and Vrbo remit directly to the county. Operators must still file a quarterly county return even when a platform collected everything. The Town of Woodstock levies no lodging tax of its own.

Does Woodstock require short-term rentals to be owner-occupied?

Not for every category, but owner-occupancy decides which one you fall into. An STR home and an STR establishment both require the owner to live on the property, and in exchange they avoid the annual night limit. A non-owner-occupied STR is permitted, yet it needs a special use permit in every zoning district, is capped at 180 days and 26 weekends a year, must have a designated local Host, and is limited to one per individual owner.

How much does a Woodstock short-term rental permit cost?

The town's permit application, revised January 2024, sets a $50 application filing fee and an annual operating fee of $400 plus $50 per bedroom. The Town Board restructured the schedule for 2025 into tiers reported at $250 plus $25 per extra room for owner-occupied in-home rentals, $350 plus $25 for owner-occupied separate structures, and $450 plus $50 for non-owner-occupied rentals. Because the Board resets fees annually, applicants should confirm the current figure with the Building Department on (845) 679-2113, ext. 13.

Last verified: July 2026. Every ordinance, tax rate, state law, and contact detail in this guide links to or comes from its official source.