StayWinterPark Trailhead Lodges

Choose from 1 to 3 bedroom units all with gourmet kitchens, gas fireplaces, private decks with outdoor seating areas and views!

Located 1/2 block from Main Street in downtown Winter Park, you can easily walk to all the shops, restaurants and is next door to the Rendezvous Event Center where plenty of festivals and live music can be enjoyed in the summer.  During the winter months, it is a wonderful area for kids to go sledding.

Trailhead Lodges is a wonderful property for families, couples and anyone wanting to enjoy the downtown area of Winter Park and the great outdoors.

Common area amenities include outdoor heated pool and hot tub, BBQ grilling area, small workout room and lounge area with pool table.

If you didn't see what you need at the Trailhead Lodges, check out our selection of Winter Park complexes  for additional lodging options to help find the right place for you! Looking for a deals too? Check our lodging specials.


Properties Available 4 properties available
This Trailhead Lodge 2 bedroom unit is great for either a winter or summer getaway to the Colorado Rocky Mountains - grab the family and fido for a luxurious getaway with a down to earth feel.The second floor unit is accessible via elevator and offers a beautifully furnished living room with large windows for views, spot to relax and enjoy the gas
Hot HOT 13
Trailhead Lodges 422
Condo - Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.8 23
Located at the Trailhead Lodges complex and on the shuttle route this property is the ultimate ski retreat for a couple, small family or 2 singles seeking comfortable accommodations. This wonderful 1 bedroom is also conveniently located next to the Rendezvous Event Center with sledding hill fit for all ages and firepits warm up. Easy walk to main
Hot HOT 11
Trailhead Lodges 731
Condo -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.9 34
Beautiful and spacious pet friendly 3 bedroom unit right from the heart of downtown Winter Park, this Trailhead Lodge unit has a wonderful view off the back deck of the Winter Park Ski Resort and downtown area of Winter Park a great place to drink morning coffee, outdoor dining area or a great spot to enjoy the evening sunsets.Families or small gro
Trailhead Lodges 131
Condo - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 9 guests
Rating 5 23
Trailhead 821 is a great spot for families wanting to enjoy the sledding hill fit for all ages and fire pits to warm up at the Rendezvous Event Center or the skate park and outdoor gymnasium in the summer. The free town shuttle access the property for the ultimate ski retreat for a couple, small family or solo travelers seeking comfortable accomm
Trailhead Lodges 821
Condo -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.8 6

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