Executive Summary
Michigan is tightening the screws on short-term rentals across multiple cities: Cheboygan capped STR permits at 12 and banned them from residential zones entirely; Dearborn is mulling a citywide residential ban; and Manistee plans to cap STRs at 165 units while adding fees and inspections. Meanwhile, West Fargo, ND, is drafting rules to limit STRs to primary residences, signaling a broader shift away from investor-owned vacation rentals in suburban markets. In Aspen, CO, changes to permit transfers and HOA restrictions are on the table, which could complicate acquisitions. And up north, Yellowknife’s new 4% tax and Highlands East’s public STR address database could increase compliance costs and scrutiny for Canadian investors. Finally, New York’s Southold Town has begun enforcing its 14-day minimum stay rule using Rentalscape software, with new short-term rental permit discussions underway.
New Regulations
Cheboygan, Michigan
Published: June 24, 2025
Regulation Category: Zoning, Licensing
Summary: Cheboygan's new ordinance limits short-term rental permits to 12 and bans them in residential areas, significantly restricting investment opportunities in those zones.
Source: Cheboygan City Council approves 2025-26 budget, new short-term rental ordinance
Southold, New York
Published: June 30, 2025
Regulation Category: Licensing, Enforcement
Summary: Southold Town's new Rentalscape software enforces a ban on rentals under 14 days, with a part-time officer aiding compliance, and a task force proposes a permitting system for rentals under 30 days.
Source: New Software Is Guiding Southold's Enforcement & Revamp of Short-Term Rental Laws
Highlands East, Canada
Published: June 26, 2025
Regulation Category: Licensing, Transparency
Summary: Highlands East will launch a public dashboard listing licensed short-term rental addresses to enhance transparency and compliance, but this could affect privacy and security.
Source: HE to make STR addresses public
Yellowknife, Canada
Published: June 29, 2025
Regulation Category: Tax, Licensing Summary: Yellowknife's new 4% tourist accommodation tax, effective April 1, 2025, requires short-term rental operators to report and submit payments by July 30, alongside maintaining a business license. Source: City of YK preps to collect tourist accommodation tax for first time
Developing Regulations
Aspen, Colorado
Published: June 25, 2025
Regulation Category: Licensing, Zoning
Summary: Aspen City Council is reviewing its short-term rental policies, potentially revising permit caps, transfer rules, and HOA approval processes. Proposed changes aim to balance revenue generation with enforcement and community concerns, with decisions expected in upcoming sessions.
Source: City Council considers refining the city's short-term rental policies
Dearborn, Michigan
Published: June 25, 2025
Regulation Category: Zoning
Summary: Dearborn is considering a ban on short-term rentals like Airbnb and VRBO in residential areas, limiting them to downtown zones with stricter regulations.
Source: Dearborn considers banning short-term rentals like Airbnb, VRBO in residential parts of city
West Fargo, North Dakota
Published: June 26, 2025
Regulation Category: Zoning
Summary: West Fargo is forming a committee to explore an ordinance limiting short-term rentals to primary residences, potentially excluding investment properties.
Source: New Short Term Rental Committee to meet for first time Monday in West Fargo
Manistee, Michigan
Published: June 29, 2025
Regulation Category: Licensing, Zoning
Summary: Manistee is reviewing a draft ordinance introducing registration fees, inspections, and a cap of 165 short-term rental units city-wide, except in overlay districts.
Source: Gateway project, short-term rental rule on city council agenda