Updated on April 29, 2025
Left: Anthony Rallo and Lindsay Bolton, Program Manager at the 2024 Spark Retreat
Right: Stonybrook State Park, Dansville, New York
Before Lindsay Bolton joined the Rent Responsibly team, she was already living the mission.
Tucked into the postcard-worthy landscapes of New York’s Finger Lakes, Lindsay was the driving force behind the Finger Lakes Vacation Rental Alliance (FLXVRA). As a grassroots effort, the alliance brought together property managers, homeowners, and local leaders to advocate for fair short-term rental policies in a region made up of more than 100 townships. It was an overwhelming undertaking, and Rent Responsibly quickly became her go-to resource.
“I started working with Alexa and the team years ago when we were trying to start our own alliance,” Lindsay recalled. “They were an incredible resource that alleviated a lot of the pain points of being a start-up group.”
Now, Lindsay is officially part of the Rent Responsibly team as a Project Manager, helping other alliances grow with the same care, dedication, and creativity she brought to the Finger Lakes community.
Homegrown STR advocacy
Born and raised just a block from the lake in the Finger Lakes region, Lindsay’s deep connection to the area started early with long summer days spent fishing, hiking, and paddling the waters that would one day become the heart of her advocacy work.
“It’s such a gorgeous area and has wonderful communities,” she said.
After stints in Tennessee and Alaska, where she gave duck boat tours and worked in cruise line tourism, Lindsay and her husband decided to return to the place that felt most like home. She took a job promoting local vineyards before making the leap into vacation rentals in 2016.
“I had never even stayed in a vacation rental when I took this position,” she said of her first role with Finger Lakes Premier Properties. “To me, I just knew that it was within the tourism realm in the Finger Lakes. And it seemed exciting.”
That spark led her to the Vacation Rental Management Association (VRMA) conference, where she discovered the broader industry she hadn’t known existed.
“I…was blown away by the energy and the people,” she said. “I’ve been hooked ever since.”
From inspiration to action
As Director of Marketing and Sales at Finger Lakes Premier Properties, Lindsay spent years monitoring local regulations, advocating for owners, and providing education and tools to STR operators across the region. In 2023, her team officially launched the Finger Lakes Vacation Rental Alliance.
“We were always being proactive and watching what was happening,” she recalled in a March 2024 interview with Rent Responsibly. “When we saw some of the regulations, the bans happening in other areas, we were like, wow, this could really affect us.”
The team’s work ranged from hosting monthly webinars, presenting STR data to town councils, and creating responsible renting resources. They even launched the Humans in Hospitality campaign and podcast to humanize hosts and bust myths about the industry.
Her efforts did not go unnoticed.
“Lindsay was one of the first alliance leader calls Dave and I took when we started Rent Responsibly,” said Alexa Nota, Co-Founder and COO. “I am so grateful she found us. She was running so far ahead of us, we were energized and inspired just trying to keep up and create things to make her advocacy work easier. She’d been on my dream team roster ever since, and I am so excited that’s now a reality.”
A natural fit
Joining Rent Responsibly felt like a full-circle moment.
“Without a doubt, the team,” Lindsay said when asked what drew her to the role. “Any time I’ve been in contact with them, their positive energy and determination to help the industry has been inspiring, and I wanted to be part of that.”
Now, she supports alliance events, communications, and logistics, helping other local leaders feel as empowered as she once did.
“So far, the most exciting part of my job has been watching the events come to fruition and seeing the engagement from attendees,” she said. “It validates how important it is for alliances to connect and share their knowledge with their regions.”
She’s still learning all the people behind the scenes but loves how approachable and helpful the team has been.
“Even in moments where I’m still learning the people and processes, the team is easily approachable with questions and very helpful,” she said.
A love of travel
Lindsay’s passion for vacation rentals stems from her own fond memories of traveling. Her favorite kind of getaway is laid-back, unplugged, and on the water.
“We plan an annual trip to the Adirondacks and stay at a different rental every year, but always on the water,” she said. “We’ve made so many great memories from kayaking and paddleboarding together and always finishing the night with some board games and s’mores at the firepit.”
One of her most memorable adventures was a summer in Ketchikan, Alaska, where she and her husband worked for local attractions and spent her days hiking, fishing, and soaking crab pods. “It was breathtaking,” she said. “I told him I wouldn’t mind returning in our retirement, but we probably won’t hike those same trails.”
When she’s not working or traveling, she’s outside with her family, hunting for sea glass, paddleboarding, or cheering on her two sons, Maddox and Owen, from the sidelines of hockey, lacrosse, and soccer games. Her dog Aspen, a fiercely protective Blue Heeler from Tennessee, often joins the backyard games.
Looking ahead
For Lindsay, being part of Rent Responsibly embraces everything she’s always loved: community, advocacy, tourism, and education.
“I’ve listened to the stories of the owners, and they have such phenomenal stories,” she said in the March 2024 interview. “Connecting with them and being a resource for them has been really rewarding.”
Stay tuned to see more of Lindsay’s behind-the-scenes work in events like Rent Responsibly’s spring 2025 RR Summit coming up on May 21, 2025.
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