About Sixteen Chairs

Homes that make room for the good things.

We’re Brenden and Brittany, the founders of Sixteen Chairs. Our story began long before the company did—we met in junior high school, married in 2021, and now live in New York with our two children and two dogs.

A trip to the Catskills sparked our interest in hospitality and inspired us to look beyond New York for our first property. That journey led us to the Poconos, where we acquired our first rental and began building what would become Sixteen Chairs.

Since then, Sixteen Chairs has expanded into the Kentucky Bourbon Trail and Indianapolis, with a focus on larger, premium homes designed for groups to gather comfortably. Across every property, we place a strong emphasis on thoughtful design, exceptional cleanliness, operational consistency, and the details and amenities that make a stay feel memorable.

Every Sixteen Chairs home is professionally designed with two goals in mind: to create a home big enough for everyone and with everything a guest needs.