Trailhead Inn is the modern basecamp to return to after a long day of adventuring on the trail, riverside or mountain. Formerly the Hotel Olympia and located in the heart of downtown Winter Park, we offer 42 rooms with a variety of lodging accommodations - from single and multi-room suites, to apartments and pet friendly options. Perfect for rejuvenating.
Trailhead Inn guests receive complimentary deluxe continental breakfast with their stay. Relax in the Inn's heated, indoor salt water pool and hot tub before heading out to grab a bite to eat or peruse the shops just minutes away in downtown. Heading over to Devil's Thumb Ranch? Hop on the Devil's Thumb Ranch Shuttle. The free shuttle runs runs on weekends and holidays and is available by reservation midweek.