First Chair on Oak | Downtown Telluride's Closest Home to the Gondola

Experience the ultimate slopeside lifestyle at First Chair on Oak, a premier luxury vacation rental in Telluride offering an unrivaled location just steps from the Telluride Gondola. With only 40 steps from your front door to the lift, this newly remodeled downtown Telluride residence places you closer to the mountain than any other home in the historic core. In winter, be the first on the slopes carving fresh powder at the world-renowned Telluride Ski Resort. In summer, stroll to the Telluride Farmers’ Market and vibrant Main Street festivals within minutes. This is true ski-in access convenience paired with effortless mountain-town living.
Inside, the home blends refined alpine design with modern comfort. Rich black wood floors extend throughout the open-concept main level, creating a seamless flow from the entry to the living space. The great room is warm and sophisticated, centered around a gas fireplace and designed with an oversized sectional, two accent chairs, and curated artwork that adds texture and character. A tucked-away chaise lounge offers a cozy retreat for morning coffee or quiet reading after a day on the mountain.
The spacious dining area comfortably seats ten guests and connects naturally to the gourmet kitchen, making it ideal for entertaining, family gatherings, and après-ski dinners. A stainless steel apron-front sink, premium stainless steel appliances, and a granite-topped island with bar seating for three elevate both style and functionality. A conveniently located powder room completes the main level.
Upstairs, the primary suite serves as a private sanctuary with vaulted ceilings, a king-sized bed, a gas fireplace, and a flatscreen TV for relaxed evenings. A dedicated seating area enhances the sense of retreat, while the spa-inspired bathroom delivers luxury at every turn. Floor-to-ceiling designer tile, dual vanities, a steam shower with dual showerheads and waterfall feature, and a separate soaking tub create a true mountain spa experience. Skylights fill the space with natural light, and a discreet workstation offers a practical touch for remote work in Telluride.
The secondary king suite, accessed via its own private staircase off the kitchen, provides added privacy for guests. Vaulted ceilings, a flatscreen TV, and an elegant en suite bath with a glass-enclosed shower make this bedroom equally inviting and comfortable.
On the lower level, a second living area is designed for relaxation and entertainment, featuring a large sectional, ottomans, and an oversized flatscreen TV—perfect for movie nights or cozy après-ski lounging. The bunk room accommodates families and groups with two twin-over-twin bunks and a separate full-size bed nook, along with an attached bath. A fourth bedroom with a queen bed and en suite bath featuring a waterfall shower completes this level. A stackable washer and dryer in the dedicated laundry room add everyday convenience for extended stays.
An upstairs west-facing patio captures sweeping ski resort views and offers comfortable seating and a fire pit, creating the perfect setting for sunset cocktails beneath alpine skies. With a private parking space in the rear, you’ll enjoy rare in-town convenience, though you may never need your car. Located at 221 South Oak, just half a block from the gondola and two blocks from Main Street, this luxury Telluride rental places dining, shopping, festivals, and outdoor adventure right outside your door.
At First Chair on Oak, you’re not simply near the action—you’re first in line for everything that makes downtown Telluride extraordinary.

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