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Legal Counsel for Short-Term Rental Owners + Hosts

Together, let’s navigate the ever-changing regulations, control the risks, and get to the opportunities in STR investing.

Host Confidently.

We've moved beyond the real estate closing to offer a suite of services tailored to the short-term rental community.

You've invested your money, time, and creativity into your properties - all to deliver five-star experiences to your guests.  Now, let's work together to make sure these investments work for you.

In addition to our menu of legal services, we have affordable general counsel plans for STR owners and co-hosts - ensuring you have an attorney available for all of your questions, even the little ones.

STR General Counsel

Have an attorney available even for your smallest questions.  Our general counsel client receive access to online attorney meetings along with proactive check-ins.  With packages designed for owners and co-hosts, we’re here for you every day.

Services include:

  • Access to online attorney meetings
  • Proactive check-ins
  • Ongoing maintenance of business entities
  • Contract review and drafting
  • Policy review and drafting
  • Discounts on other legal services and projects
Real Estate Transactions

Buying, selling, or refinancing real estate is a momentous day for anyone.  Whether you’re purchasing your first home or adding to your portfolio, let us handle the closing and ensure it’s done correctly.

  • Services include:
  • Purchase, sale, and refinance closings
  • Contract review and drafting
  • 1031 Exchanges
  • Creative and seller financing transactions
  • Deed transfers
  • Title resolution
Business Entities & Asset Protection

Your STR investments should work for you.  That’s why we work with our clients to set up the right business entities, limit personal liability, and strategize for taxes.  Once established, we’ll work together to maintain the businesses correctly and collaborate on best practices.

Services include:

  • Strategic entity planning
  • Creation of LLCs and corporations
  • Creation of trusts
  • Asset protection and insurance counsel
  • Ongoing maintenance of business entities
State & Local Compliance

Local communities are constantly changing the rules for short-term rentals, always throwing more uncertainty into your hosting business.  We’re here to navigate these complexities with you - understanding the law, getting the right permits, and advocating for your rights.

Services include:

  • Review of local regulations
  • Review of HOA regulations
  • State & local permit applications
  • State & local appeals
  • Enforcement defense
Dispute Resolution

When problems strike, we’re trusted counsel and tireless advocates for STR operators.  Whether in court or not, we’ll protect your interests, mitigate your risks, and open new opportunities.

Services include:

  • Pre-litigation counsel and representation
  • Enforcement defense
  • STR-related litigation
  • OTA disputes
  • Other creative problem solving
Estate Planning

Your STR investments are a key component of your legacy.  Let’s protect your life’s work and your loved ones through estate planning tailored to the STR owner and real estate investor.

Services include:

  • Will and trust drafting
  • Estate and tax planning
  • Estate plan modifications

Meet Attorney Rory Gill

Directly out of law school, I started my law practice with a focus on my neighbors and community.  With that mission, I counseled clients on a wide range of matters - real estate transactions, land use permitting and appeals, litigation, estate planning, and more.  These diverse areas were connected by a common goal of helping clients constructively grow their wealth and achieve their goals - mostly within real estate.

While running the law practice practice, I found a new creative outlet in short-term rental investing. Starting with a house in my family’s lakeside neighborhood, my husband and I now own five STRs in Massachusetts and New Hampshire. When I claim to understand the joys, challenges, and opportunities in STR investing, it’s because I’ve lived it myself. Finding property, designing homes, and building effective systems have been a rewarding experience - one that’s helped my family achieve financial freedom. That’s why I’m proud to provide my peers the legal counsel and confidence needed to grow their own STR investments and businesses.

After many years in South Boston, I now live with my husband and young daughter in Newburyport.  

  • Licensed in Massachusetts and New Hampshire
  • JD 2011, Northeastern University School of Law
  • BA 2006, Boston University

Latest Episodes from the SmartStay Show

Welcome to the SmartStay Show, where profit meets strategy for short-term rental hosts. Hosted by STR.Legal Attorney Rory Gill and 30-time Airbnb Superhost Jason Muth, this podcast is your go-to resource for mastering the world of vacation rentals on platforms like Airbnb and Vrbo.

Each episode is packed with actionable tips and real-life strategies designed to help you maximize your income while safeguarding your property. Whether you're just starting out or looking to enhance your existing listings, the SmartStay Show covers everything from pricing optimization and guest communication to legal compliance and automation tools. With expert advice from seasoned hosts and industry insiders, we provide the playbook for turning your rental into a top-performing asset.

What sets us apart is our focus on owners of small but mighty portfolios. You don’t need to own dozens of properties to succeed — we specifically cater to hosts who self-manage and want to get the most out of their vacation rentals.

Betting on Yourself + Leaving a Lucrative Career for STRs (WAS IT WORTH IT?) - with Payton Cummings

Payton Cummings shares her journey from corporate consulting to full-time entrepreneurship and the mindset shifts that made it possible.

Want to Scale Your Airbnb Portfolio? Stop Doing Everything Yourself! - with Jayla Siciliano

In this episode of SmartStay Show, Jayla Siciliano takes us through her journey to building a thriving short-term rental business across multiple states.

Turn Your Airbnb into a Money-Making Machine with These Upgrades - with Mark Lumpkin

In this episode of SmartStayShow, we uncover the secrets behind top-performing vacation rentals with Mark Lumpkin, sales director at STRCRIBS.

They’ve Stayed in 33 Airbnbs – Here’s What Hosts Get RIGHT! - with Marissa + Eric Dingler

We sit down with Eric and Marissa Dingler, a family that sold most of their possessions and turned their home into a life of adventure.

His HELOC Strategy Made STR Investing Easy (Smart Money Move!) - with Jim McGowan

Jim McGowan, a seasoned sales professional, has successfully built a profitable short-term rental portfolio—all while maintaining his full-time job!

Airbnb Hosts: This Simple AI Tool Saves You HOURS Every Week! - with Jay Ullrich

Jay Ulrich, CEO and co-founder of HostBuddy.ai, explores how AI is revolutionizing short-term rental management.

THRIVE With Hard Money Lending and Scale Your Airbnb Empire (Here's How!) - with David Little

David Little, co-founder of Crown Capital Resources, explores how savvy investors are using short-term rentals as a game-changing exit strategy.

How I Fought Back Against Bad Airbnb Reviews (And Won!) - with Islam Elgarhi

Islam Elgarhi, an STR investor and entrepreneur, explains how he turned a chance discovery into a thriving business and AI tool combatting bad reviews.

Is Bad Guest Communication Hurting Your 5-Star Reviews? - with Kory Himmer + Alex Steeg

Alex Steeg and Kory Himmer of SmartStay Coaching dive into the game-changing power of proactive communication in short-term rental hosting.

Everything You THINK You Know About Hostels Is Wrong - with Howzit Hostels Co-Founder Nathan St Cyr

Nate St Cyr, the visionary co-founder of Malama Capital and Howzit Hostels, discusses how he’s revolutionizing the traditional hostel concept in Hawaii.

Our $130k Water Damage Claim - How Proper Insurance Saved Our STR Lake Home! - with Darren Pettyjohn

Darren Pettyjohn, co-founder of Proper Insurance, unpacks why short-term rental insurance is so crucial and how their specialized coverage works for hosts.

NEVER Overlook This in Your Airbnb Design (Insider Tips) - with Dre Shapiro

With her incredible design sensibilities, Dre Shapiro discovered Joshua Tree, turned it into her own, and transformed her home into a guest favorite.

How BiggerPockets’ STR Expert Stays Fully Booked Year-Round - with Garrett Brown

Garrett Brown, the short-term rental resident expert at Bigger Pockets, shares his journey from hospitality to real estate success.

The Genius Solution for Family-Friendly Airbnbs (No Gear Required!) - with BabyQuip CEO Fran Maier

Fran Maier, CEO of Baby Quip, explores how providing essential baby and toddler gear can elevate the guest experience.

The Truth About Direct Bookings for Serious Airbnb Hosts - with Abby Grous

Abby Grous, the Senior Product Manager of Direct at Hospitable explores the power of direct bookings.

Remote Hosting Secrets Every Airbnb Host Should Know! - with Punith Upadhya

Punith Upadhya, the mastermind CEO of Moon Gaze Stays, who’s figured out how to run a world-class short-term rental operation from hundreds of miles away

Airbnb Guests Are Paying MORE for Vintage + Local Vibes - Here’s Why! - with Christina Melander

Christina Melander, founder of Knotty Pine Design and a talented short-term rental host, discusses her blend of budget-conscious and authentic design

How Proper Signage Can SAVE Your Airbnb from Bad Reviews

Importance of signage in short-term rentals to reduce guest questions and enhance the guest experience.

The Ultimate Airbnb DESIGN Hacks + Pro PHOTO Tips That Hook Potential Guests - with Justin Miller

Justin Miller, co-founder of Showplace and a true trailblazer in hospitality design

How to Handle Airbnb Guests + Issues Without Being On-Site - with Jarrett Chouinard

Jarrett Chouinard, the founder of Stellar Retreats, who shares his inspiring journey into the short-term rental world

Say Goodbye to Strangers Renting Your Second Home - with Brent Hieggelke

Brent Hieggelke, the visionary founder of Trustr, a groundbreaking platform redefining the short-term rental experience.