StayWinterPark Trailhead Lodges

Resort StayWinterPark Trailhead Lodges winter exterior
Resort StayWinterPark Trailhead Lodges winter exterior Winter exterior of building
Resort StayWinterPark Trailhead Lodges living room Living room
Resort StayWinterPark Trailhead Lodges dining area Dining room
Resort StayWinterPark Trailhead condos living room Living room
Resort StayWinterPark Trailhead Lodge Kitchen
Resort StayWinterPark Trailhead Lodges bedroom Bedroom
Resort StayWinterPark Trailhead condos bedroom Bedroom
Resort StayWinterPark Trailhead Lodges living room
Resort StayWinterPark Trailhead Lodges bedroom
Resort StayWinterPark Trailhead lodge Clubhouse BBQ area, pool and hot tub
Resort StayWinterPark Trailhead Lodges summer exterior Summer exterior of property
Resort StayWinterPark Trailhead Lodges swimming pool

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

Situated just half block from the Main Street in downtown Winter Park, you can conveniently stroll to all the shops, restaurants and is adjacent  to the Rendezvous Event Center where numerous festivals and live music can be enjoyed in the summer.  In the winter, it is an ideal area for children to go sledding.

Trailhead Lodges is an exceptional property suitable for families, couples and anyone looking to experience the downtown area of Winter Park and the beautiful outdoors.

On-site amenities include outdoor heated pool and hot tub, BBQ grilling area, small workout room and a lounge area with pool table.

If you haven't found what you're looking for at the Trailhead Lodges, explore our range of  Winter Park complexes  for additional lodging options to help you find the perfect place for your stay! Interested in special deals? Be sure to check our lodging specials.

Properties Available 4 properties available
This two bedroom unit at Trailhead Lodge is ideal for a winter or summer retreat in the Colorado Rocky Mountains. Gather your family and furry friend for a luxurious yet approachable escape.The unit located on the second floor can be reached by elevator and features a tastefully decorated living room with expansive windows that provide scenic view
Specials Tag Special
Stay Longer in Winter Park, Save Bigger

Sink into vacation mode in the Fraser Valley and Winter Park area and enjoy 20% off 7–21 night stays with promo code LTR26. Travel between April 14 and December 18, 2026, and book by December 10, 2026, to lock in your savings.*

Looking for something beyond a three-week stay? We'll help you plan a longer stay that works for you, contact us at (800) 215-6535 or [email protected] to inquire about flexible options and best pricing.

*Offer is valid on new online bookings when you book by December 10, 2026, for length of stays between 7 and 21 days between April 14 and December 18, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.


Trailhead Lodges 422
Trailhead Lodges 422
Condo - Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 100
View Property Details
Situated within the Trailhead Lodges complex and conveniently positioned along the shuttle route, this property serves as the ideal ski getaway for couples, small families or two individuals in search of cozy accommodations. This delightful one bedroom unit is also in close proximity to the Rendezvous Event Center, which features a sledding hill s
Specials Tag Special
Stay Longer in Winter Park, Save Bigger

Sink into vacation mode in the Fraser Valley and Winter Park area and enjoy 20% off 7–21 night stays with promo code LTR26. Travel between April 14 and December 18, 2026, and book by December 10, 2026, to lock in your savings.*

Looking for something beyond a three-week stay? We'll help you plan a longer stay that works for you, contact us at (800) 215-6535 or [email protected] to inquire about flexible options and best pricing.

*Offer is valid on new online bookings when you book by December 10, 2026, for length of stays between 7 and 21 days between April 14 and December 18, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.


Trailhead Lodges 731
Trailhead Lodges 731
Condo -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.9 137
View Property Details
Trailhead 821 is an excellent destination for families and is pet friendly, offering a sledding hill suitable for all ages, as well as fire pits for warming up at the Rendezvous Event Center. In the summer, visitors can enjoy the skate park and outdoor gymnasium. The property is conveniently accessible via the free town shuttle, making it an idea
Specials Tag Special
Stay Longer in Winter Park, Save Bigger

Sink into vacation mode in the Fraser Valley and Winter Park area and enjoy 20% off 7–21 night stays with promo code LTR26. Travel between April 14 and December 18, 2026, and book by December 10, 2026, to lock in your savings.*

Looking for something beyond a three-week stay? We'll help you plan a longer stay that works for you, contact us at (800) 215-6535 or [email protected] to inquire about flexible options and best pricing.

*Offer is valid on new online bookings when you book by December 10, 2026, for length of stays between 7 and 21 days between April 14 and December 18, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.


Trailhead Lodges 821
Trailhead Lodges 821
Condo - Pet Friendly
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.9 130
View Property Details
This charming and expansive pet friendly three bedroom unit is located in the very center of downtown Winter Park. The Trailhead Lodge unit offers a stunning view from the back deck overlooking the Winter Park Ski Resort and downtown area. It serves as an excellent location for enjoying morning coffee, featuring an outdoor dining area and provide
Specials Tag Special
Stay Longer in Winter Park, Save Bigger

Sink into vacation mode in the Fraser Valley and Winter Park area and enjoy 20% off 7–21 night stays with promo code LTR26. Travel between April 14 and December 18, 2026, and book by December 10, 2026, to lock in your savings.*

Looking for something beyond a three-week stay? We'll help you plan a longer stay that works for you, contact us at (800) 215-6535 or [email protected] to inquire about flexible options and best pricing.

*Offer is valid on new online bookings when you book by December 10, 2026, for length of stays between 7 and 21 days between April 14 and December 18, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.


Trailhead Lodges 131
Trailhead Lodges 131
Condo - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 9 guests
Rating 5 256
View Property Details

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