In-depth analysis

Should you buy an STR in Woodstock in 2026?

Conditionally. Woodstock is a low-priced point of entry into the Catskills STR market with a durable cultural-tourism brand. ADR $157, occupancy 56%, RevPAR $88, market score 56/100. The town has been tightening STR rules in response to neighborhood pushback — verify current posture before offer.

Regulation: where the city stands

Town of Woodstock STR rules:

STR permit / annual registration required, with primary-residence and second-home distinctions.
Density / parking rules vary by zoning district.
Ulster County room-occupancy tax stacks on New York State sales tax — total around 12-14%.
New York State STR registry (in development; pilot in NYC, broader rollout pending) adds a state-level disclosure layer.

Note: Woodstock the town is in Ulster County, NY — not Vermont. The Woodstock ‘69 festival was actually held in Bethel, NY, but the cultural-tourism brand attaches to the town. Bearsville, West Hurley, Saugerties (nearby separately governed) have their own STR rules.

The market by the numbers

Metric	Woodstock	Comparison
Avg ADR	$157	Modest Catskills
Occupancy	56%	Weekend-driven
RevPAR	$88	Thin
Market score	56/100	Below average

Demand: weekend escapes from NYC (2.5-3 hours), summer arts festivals, fall foliage, winter skiing at Hunter and Belleayre (nearby). Weekday occupancy is materially lower than weekend.

Submarkets that matter

Woodstock Village — walkable Tinker Street, premium ADR, parking-restricted.
Bearsville / Wittenberg — wooded SFR, cabin product, family demand.
Bythe Hollow / Glasco Turnpike — rural, longer drive to town, cheaper basis.
Saugerties (adjacent) — different town, different STR rules, Hudson River access.

The 3 mistakes buyers make here

Underwriting weekday occupancy at weekend rates. Friday-Saturday-Sunday is the demand. Reserve cash for weekday softness.
Confusing Woodstock with Saugerties or Bearsville. Each town governs separately.
Buying without checking the current Town of Woodstock STR ordinance. Rules have tightened in recent years and continue to evolve.

What to do next

Pull the Town of Woodstock STR rules and confirm posture.
Verify Ulster County occupancy-tax registration.
Run Market Score and Comp Analyzer.
Track the New York State STR registry rollout.

Not investment advice. Verify all regulatory and tax information with local authorities and licensed professionals before committing capital.