About Telluride Luxury Rentals + Real Estate Inc.
Since 1992, Telluride Luxury Rentals + Real Estate has been the premier full-service real estate and vacation rental company in the Telluride region. As a boutique, owner-operated business with deep roots in the community, we pride ourselves on offering unparalleled service, attention to detail, and local expertise to all new guests, second homeowners, and locals alike.
Whether you’re searching for a luxury slope-side Mountain Village home, a chic ski-in/ski-out condo, or a romantic getaway with world-class dining and spa treatments, we are your trusted partner in creating unforgettable Telluride experiences. For those ready to make Telluride their forever home, we specialize in helping you navigate the local market with confidence—whether it’s purchasing a single-family home, a condo, or a piece of land to build your dream retreat.
Our team is committed to making every interaction seamless and tailored to your unique needs. With decades of experience, we handle everything from the initial search to the final details, providing 24/7 complimentary concierge services with every vacation rental. No matter your vision, we’re here to make it a reality.
Telluride is more than a destination; it’s a lifestyle—and we’re here to help you discover the best it has to offer. Contact us today to begin your next adventure or find your dream home in this breathtaking corner of the world.
Telluride Luxury Rentals + Real Estate Inc. Staff
Meet Rosie!
Owner Rosie Cusack created Telluride Luxury Rentals and Real Estate in 1992 and grew the business into the comprehensive real estate and vacation rental resource it is today. Representing a plethora of property owners and an impressive roster of real estate clientele, Telluride Luxury Rentals and Real Estate is the go-to real estate company and one stop shopping vacation planner to meet all your needs.
Looking for a weekend getaway? Looking for a more adventurous vacation pushing outdoor activity to the max? A romantic Valentine’s Day Weekend? Or a glorious, luxurious vacation with daily spa treatments and superior cuisine options? Telluride Luxury Rentals and Real Estate has the perfect property to meet each and every one of the most discerning travelers needs! Please feel free to review the properties we representon behalf of owners or for a comprehensive response, complete an inquiry form and we will reply with any and all options available throughout Telluride to meet your needs. Look no further! We are an owner operated boutique rental and real estate business. Attention to detail and personal 24/7 complimentary concierge service comes with every Telluride Luxury Rentals and Real Estate booking. We are here to be your first and last resource for your next amazing vacation.
Looking to buy or sell a home in the Telluride Region? Helping clients purchase and sell homes is what Rosie has been doing for over thirty years. Telluride Luxury Rentals and Real Estate has the local knowledge and expertise to make the process as easy and quick as possible. Whether you are looking to purchase a jaw-dropping log home in Mountain Village or ready to sell your modest condominium in Telluride, Rosie will help. Let Rosie use her years of market experience to help make your home buying or selling as seamless and worry-free as can be.
Ryan “RED” Higgins
Broker Associate
Ryan was born and raised in Buffalo, New York, and moved to Telluride in 2016 after graduating from the State University of New York at Geneseo. Joining Rosie Cusack and Telluride Luxury Rentals & Real Estate was the perfect segue after studying geography with a focus in real estate analysis. Ryan has found himself taking pride in helping buyers and sellers navigate the region’s real estate market. When Ryan isn’t working with clients, he enjoys skiing, mountain biking, hiking, and coaching youth hockey.
Lauren Oliver
Director Of Operations
Lauren Oliver grew up in New York and earned her Master’s degree in Occupational Therapy from the University at Buffalo. In 2015, she relocated to Telluride, drawn by a desire to be closer to the mountains and an active, outdoor-focused lifestyle.
Over the years, Lauren has built a diverse professional background spanning occupational therapy, restaurant and hospitality management, administrative operations, and crisis services. This wide-ranging experience has shaped her strong organizational skills, people-first approach, and ability to adapt in fast-paced, dynamic environments.
Lauren joined Telluride Luxury Rentals and Real Estate in the summer, bringing with her a deep appreciation for service, communication, and thoughtful problem-solving. Her varied career path allows her to connect easily with property owners, guests, vendors, and team members alike, ensuring operations run smoothly and with care.
Outside of work, Lauren is passionate about skiing, hiking, camping, and traveling, and values the balance between hard work, adventure, and community that life in Telluride offers.
Email: laureno@tellurideluxury.co
Phone: 970-708-1699
Whitney Chadwick
Property Manager
Whitney Chadwick is a detail‑oriented property management professional
with a strong background in hospitality, logistics, and client service.
With years of experience leading high‑end bar programs, managing inventory,
and delivering exceptional guest experiences, she brings precision,
organization, and a people‑first approach to every property she oversees.
Her extensive travel‑planning experience coordinating complex,
multi‑country itineraries further strengthens her skills in scheduling,
vendor coordination, and problem‑solving. Whitney combines operational
expertise with a calm, solutions‑driven mindset to ensure smooth operations
and an elevated experience for residents and partners alike.
Email: whitney@tellurideluxury.co
Phone: 970-239-1388
Kevin Gilleland
Head of Maintenance
Kevin serves as Head of Maintenance at Telluride Luxury, overseeing the
care and upkeep of the company’s portfolio of luxury homes and properties.
Raised in the Black Hills of South Dakota, he developed hands-on experience
early through his family’s HVAC and mold remediation business, construction
work during college, and a lifelong passion for mechanical work and repairs.
After discovering Telluride in 2016 and relocating full-time in 2022, Kevin
has become a trusted in-house resource known for his proactive approach,
problem-solving abilities, and attention to detail. He works closely with
owners, vendors, and the Telluride Luxury team to ensure properties are
maintained to the highest standard for both owners and guests. Outside of
work, he enjoys snowboarding, paddle boarding, and spending time outdoors
with his dog, Jax.