Chat with us
1 Guests
1 Bedrooms
Filters

Trailhead Lodges Vacation Rentals in Winter Park

Trailhead Lodges is a bustling condo community located in downtown Winter Park. Known for its convenient location and amenities catering to outdoor enthusiasts and visitors to the area, here are a few reasons why we LOVE Trailhead Lodges!

Location: Situated in the heart of Winter Park, Trailhead Lodges offers easy access to the ski slopes of Winter Park Resort, as well as nearby hiking and mountain biking trails. It's also close to restaurants, shops, and other attractions in the area.

Accommodations: The condos at Trailhead Lodges range from cozy one-bedroom units to spacious multi-bedroom layouts, providing options for couples, families, and groups. Many condos feature modern mountain-inspired decor, fully equipped kitchens, fireplaces, and balconies or patios with scenic views of the surrounding mountains.

Amenities: Trailhead Lodges offers a range of amenities to enhance guests' stay, including:

  • Year-round, outdoor heated swimming pool and hot tubs that are perfect for relaxing after a day of outdoor activities. This is one of the only year-round pools in Winter Park!
  • The large fitness center is equipped with cardio machines and weights for guests to maintain their fitness routines.
  • A communal clubhouse where guests can gather, featuring a fireplace, seating areas, and games like pool and foosball.
  • Convenient storage space for ski equipment during the winter season.
  • Location, Location, Location! Winter Park hosts a range of events and festivals throughout the year, and Trailhead Lodges is ideally situated for guests to enjoy these festivities, most of them taking place at the Rendezvous Events Center at Hideaway Park which is right across the street. From music festivals to food and wine events, there's always something happening in the area.

Our Trailhead Lodges vacation homes have been carefully decorated to offer a personalized feel, plus a variety of sleeping configurations to suit different sizes of groups. Plus, quite a few of these condos are pet-friendly which means you can bring Fido to your favorite mountain town!


  • 10 properties returned
  • Sort by: Beds (ASC)