Brenden and Brittany, owners of Sixteen Chairs, with their dog

About Sixteen Chairs

Homes that make room for the good things.

We’re Brenden and Brittany, the founders of Sixteen Chairs. We met in junior high school and got married in 2021. We live in New York with our two children and two dogs. After a trip to the Catskills, we were inspired to enter hospitality outside of New York and acquired our first rental in the Poconos.

Sixteen Chairs has since grown into the Kentucky Bourbon Trail and Indianapolis, Indiana, focusing on larger, upscale group stays. We pride ourselves on operational excellence, cleanliness, fine details, and amenities that leave our guests wanting to come back.

Every home is professionally designed to help you settle in, slow down, and feel at home.

The collection

Our properties.

Big enough for everyone you're bringing.