Sales & Guest Services Team

When Bennington Properties started in 1998 it had only one employee, Penny Bennington's sister Carolyn.  Over the years we have been very fortunate to have some incredible people join our team.  All of our associates are not only hard working, caring people but they are also very talented.  We owe our success to these individuals and are so grateful to call them our colleagues.

Meet the Team

Chatta @ Bennington Properties, Vacation Planner


Vacation Planner Chatta Tsuchiguchi has worked for Bennington Properties since 2007. She moved up to Central Oregon from a town just south of San Jose; Morgan Hill, California. An impromptu ski trip to Mount Bachelor led her away from the sunny confines of her Northern California home and introduced her to a seemingly whole new world.

“The beauty and diversity of Central Oregon was as unexpected as it was thrilling. The air was so crisp and the colors so vivid, I felt as if I had been living in a black and white world.”

Learn more about Chatta

Jess Rae McIntyre, Vacation Planner


Vacation Planner Jess Rae McIntyre joined the Bennington Properties team in late August, 2015. Jess Rae brings with her a background in the vacation rental business as well as small business ownership.

Jess Rae grew up in San Luis Obispo, California alongside two sisters and a brother. After high school, she joined the United States Navy. The Navy took her to Hawaii for three years, then Guam for six and a half years and finally San Diego for six years.

Learn more about Jess Rae

Gina @ Bennington Properties, Marketing & Communications Coordinator


Gina has been a part of the Bennington Properties team for five years. In fact, she was our Christmas gift to ourselves, with her first day of work being on Christmas Eve! She manages the Bennington Properties email marketing campaigns, social media accounts, blogs, and most marketing promotions. We are proud to take advantage of Gina’s over two decades in the travel industry.

Originally from Burney, California, Gina grew up in Oakridge and Salem, Oregon. She spent her childhood enjoying the life of a close-knit small family atmosphere in a country rural town. After graduating from high school in Salem, Gina became a second generation Beaver by attending Oregon State University. To this day, she remains an ardent supporter of the OSU Beavers!

Learn more about Gina

Ohana Bennington, VP of Pet Relations​


As official greeter, nap-location tester, and purveyor of happy thoughts, Ohana Bennington makes up the core of Bennington Properties. She loves her job and all of her co-workers, especially the ones who remember to bring treats.

Ohana was born January 12th, 2014, in Willamette Valley’s Woodburn, Oregon, to attentive parents and a nice lady named Gina. Her new family, the Benningtons, were anxious for her arrival and very excited when she was born. They called her by a beautiful name, Ohana, which means family. The name is perfect for her because it alludes to the Bennington’s connection to Hawaii, highlights the family business that serves families, and proves the fact Ohana is not a pet, but rather a part of the family.

Learn more about Ohana

Kipa Bennington, Head Ranger, Camp Bennington


Kipa is the Head Ranger for Camp Bennington.  Kipa loves it when kids explore the amazing world of Sunriver.  From Sunriver's rich human and natural history to its amazing plant and animal life, Kipa wants you to experience it all. 

Kipa's name comes from the Hawaiian word "ho'okipa."  In the Hawaiian language, ho'okipa means hospitality, friendliness, generosity, and taking care of others.  The culture and traditions of the Hawaiian people have been an important part of Kipa's family for many generations. 

If you are 12 or under, don't forget to ask for your Camp Bennington Ranger Guide.

Learn more about Kipa

Kelly Riley-Jones, Office Administrative Assistant


Administrative Assistant Kelly Riley-Jones has worked for Bennington Properties since 2009. She started at our front desk, and has worked her way up to since. Prior to coming to Bennington Properties, Kelly was a letter carrier for the United States Postal Service in Salem. Kelly and her husband Rick used to visit Sunriver every February and quickly fell in love with the area. They bought a house here for retirement and put it in our rental program until they were ready to move here. When they finally moved out for Rick’s retirement in 2009, Kelly decided to take a job with us!

Learn more about Kelly

Jan Tuckerman, Guest & Owner Representative


For over 24 years, Guest & Owner Representative Jan Tuckerman has been a resident of Sunriver. We think that makes her an expert on all things Sunriver. She applies that knowledge to happily assisting both rental owners and guests.

“Every day in Sunriver is another day in Paradise!”

Jan was born and raised in the Cleveland area, but includes Chicago, Southern California, Northern California, and Portland, OR on her list of past residences. Prior to working in the vacation rental field, Jan held many different and fascinating jobs— math teacher, criminal prosecutor, nuclear medicine technologist and brewery tour guide.

Learn more about Jan

Haylie Collins, Guest & Owner Representative


Haylie has been a part of the Bennington Properties Guest and Owner Services Team since June of 2017. She was born, raised, and lived all her life within 20 minutes of Sunriver. Haylie grew up in a family with two brothers and two sisters. Now, she has a child of her own, and fills her house with four dogs. Her knowledge of Central Oregon makes Haylie an invaluable member of our team.

“I am a big people person. I love meeting new people and although I am shy, it's still nice to see new faces and come out of my shell.”

Learn more about Haylie

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