Entire condo

☜ DOWNTOWN DIGS | Stay By The Park & Skiing | Trailhead Lodges 424 | Walk Everywhere

Photo gallery for ☜ DOWNTOWN DIGS | Stay By The Park & Skiing | Trailhead Lodges 424 | Walk Everywhere

A lodge with multiple floors, a central courtyard, and a pond. - ☜ DOWNTOWN DIGS | Stay By The Park & Skiing | Trailhead Lodges 424 | Walk Everywhere (Winter Park)
A riverside park with a pond, picnic tables, and a red-roofed building with outdoor seating. - ☜ DOWNTOWN DIGS | Stay By The Park & Skiing | Trailhead Lodges 424 | Walk Everywhere (Winter Park)
A lodge with multiple buildings, outdoor seating, and a mountain backdrop. - ☜ DOWNTOWN DIGS | Stay By The Park & Skiing | Trailhead Lodges 424 | Walk Everywhere (Winter Park)
An outdoor patio with a fire pit, barbecue grills, and outdoor seating. - ☜ DOWNTOWN DIGS | Stay By The Park & Skiing | Trailhead Lodges 424 | Walk Everywhere (Winter Park)
A park with red swings and a fenced area. - ☜ DOWNTOWN DIGS | Stay By The Park & Skiing | Trailhead Lodges 424 | Walk Everywhere (Winter Park)
Take advantage of an arcade/games room, laundry facilities and a gym at ☜ DOWNTOWN DIGS | Stay By The Park & Skiing | Trailhead Lodges 424 | Walk Everywhere. For some rest and relaxation, visit the hot tub. Guests can connect to free in-room WiFi.

Reviews

9.4 out of 10
Exceptional

Popular amenities

  • Hot tub
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Gym

Add dates for prices

About this property

☜ DOWNTOWN DIGS | Stay By The Park & Skiing | Trailhead Lodges 424 | Walk Everywhere

  • Trailhead Lodges 424 is a gorgeous condo with a plethora of amenities including a clubhouse with a gym, heated pool, hot tub, and a communal area with gas grill & fire pits. This home also has a private washer and dryer, and a full spacious kitchen with high-end finishes. The comfortable living room with modern leather furniture boasts a fireplace and a flat screen, plus forest views and a private balcony. This two-bedroom condo is located in an enviable location in one of downtown Winter Park's most popular complexes. This is a prime location downtown, close to Hideaway Park and just a few minute walk to your choice of shops and restaurants. You'll love your stay at Trailhead Lodges 424, which has everything you need for your mountain adventures.

    Sleeping Arrangements: Primary King Suite, Full/Full bunk and Twin single in the bunk room, and a Queen pullout couch in the living room. Sleeps up to seven guests.

    Local Deals: Save on local adventurous activities, gear rentals, transportation, and more when booking with us.

    Please Note:
    - Quiet hours begin daily at 10pm. Please respect your neighbors, many of which live nearby year-round.
    - This condo is in building 4 on level 2.
    - This home does not have air conditioning, but there is a ceiling fan or portable fan in each room.

    Luxury Linen Package Included: This home has crisp, white duvet covers that are washed after every stay. Enjoy hotel-style bedding in the comfort of a home.

    Parking: There is room for two cars in any open areas around the building.

    Location: Trailhead Lodges is located in the center of downtown Winter Park. Just 2 miles to Winter Park Resort and a short, easy walk to shops, restaurants and the free shuttle service in downtown Winter Park.

    RENTAL LICENSE NO: 017114

    The Winter Park Lodging Company Difference

    24/7 Local Help: Book with confidence knowing that the rates, images and details published on this property are 100% accurate. We are conveniently headquartered in Winter Park, this provides us with a local advantage to take care of any issue or need that may arise during your stay, 24/7. If any questions, needs or concerns arise just call us and we will be there at your door to make it right.

    Keyless Lock: This home is equipped with a Smart Lock, allowing easy, secure access to your property at check-in and throughout your stay. There's no need to check in at a separate location!

    What's Included: Every home is stocked with all your household essentials, high quality sheets and towels, and a starter kit of high-end bathroom products, and an ample supply of laundry detergent, trash bags, dish soap, tissues, etc.

    We're Following the Rules: This vacation rental is professionally managed and follows all local & state tax rules. Your reservation total includes all applicable taxes, cleaning fee, and Accidental Property Damage Protection.

    Clean & Safe: Keeping our vacation homes sparkling clean is a top priority at Winter Park Lodging Company. All properties are cleaned, sanitized & disinfected before guests check-in with products proven to eliminate viruses & bacteria. All linens are laundered at an offsite facility that meets commercial standards. Additionally, the entirety of our housekeeping processes meet and exceed CDC cleaning guidelines. If you have any questions/concerns, please reach out to our Vacation Planners for more details.

    Check-In: This property offers remote check-in upon arrival. Check-in instructions will be sent via email within 48 hours of check-in date once the Rental Agreement is signed.

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About the area

Located in Winter Park, this condo is in the city centre and in the mountains. Byers Peak Wilderness and Hideaway Park reflect the area's natural beauty and area attractions include Amaze'n Maze Winter Park and Alpine Slide. Enjoy the area's slopes with cross-country skiing and snowboarding, and don't miss out on the ice skating and sledging. Visit our Winter Park travel guide
View more Condo rentals in Winter Park
Map
Winter Park, CO

What's nearby

  • A mountainous landscape with a town nestled in a valley. Snow-capped mountains and a clear blue sky are visible in the background.
    Winter Park Visitor Center
    3 min walk - 0.3 km
  • Hideaway Park
    1 min walk - 0.1 km
  • Bella Vita
    5 min walk - 0.5 km
  • Blue Sky Massage
    7 min walk - 0.6 km
  • Grand Park Community Recreation Center
    18 min walk - 1.5 km

Getting around

  • Fraser/Winter Park Station
    5 min drive
  • Broomfield, CO (BJC-Rocky Mountain Metropolitan)
    97 min drive

Restaurants

  • McDonald's
    5 min walk
  • Sharky's
    6 min drive
  • The Smokehouse BBQ
    7 min walk
  • Wendy's
    5 min drive
  • Hernando's Pizza Pub
    16 min walk

Frequently asked questions

Is ☜ DOWNTOWN DIGS | Stay By The Park & Skiing | Trailhead Lodges 424 | Walk Everywhere pet-friendly?

No, pets are not allowed at this property.

How much is parking at ☜ DOWNTOWN DIGS | Stay By The Park & Skiing | Trailhead Lodges 424 | Walk Everywhere?

On-site parking is available at the property.

What time is check-in at ☜ DOWNTOWN DIGS | Stay By The Park & Skiing | Trailhead Lodges 424 | Walk Everywhere?

Check-in begins at 4:00 PM.

What time is check-out at ☜ DOWNTOWN DIGS | Stay By The Park & Skiing | Trailhead Lodges 424 | Walk Everywhere?

Checkout is at 10:00 AM.

Where is ☜ DOWNTOWN DIGS | Stay By The Park & Skiing | Trailhead Lodges 424 | Walk Everywhere located?

This family-friendly Winter Park condo building is located in the mountains, within a 5-minute walk of Hideaway Park and Winter Park Visitor Center. Bella Vita and Blue Sky Massage are also within 10 minutes.

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Reviews

☜ DOWNTOWN DIGS | Stay By The Park & Skiing | Trailhead Lodges 424 | Walk Everywhere Reviews

9.4

Exceptional

9.6

Cleanliness

9.8

Location
Rating 10 - Excellent. 42 out of 50 reviews
Rating 8 - Good. 4 out of 50 reviews
Rating 6 - Okay. 1 out of 50 reviews
Rating 4 - Poor. 1 out of 50 reviews
Rating 2 - Terrible. 2 out of 50 reviews

Reviews

From a partner site

10/10 Excellent

Great place

Staff was very responsive to questions and issues and very friendly and accommodating. We had a great time at the condo and in town
From a partner site

10/10 Excellent

Holiday season stay

Great place to stay perfectly located to so many activities. Customs service alone was enough to come back soon.
From a partner site

10/10 Excellent

Excellent

Great service and lodging. Only have good things to say.
From a partner site

8/10 Good

Above Average

Very comfortable and clean thank you
From a partner site

10/10 Excellent

Winter Park Stay - January 2024

Good layout and view of natural landscape in the back. Good proximity to the pool and hot tub. Kitchen utensils and gadgets were above average. Closet space for hanging clothes in bedrooms was limited. Overall, was clean and relatively modern.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Nice place
Stayed 4 nights in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Absolutely incredible stay. 10/10. The management was so responsive and easy to contact and so so helpful.
Stayed 4 nights in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
While there was a slight issue, they resolved it quickly and the accommodations were excellent!
Stayed 3 nights in Jan 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place, great location. We took advantage of being able to walk around town. The kids enjoyed the small sledding hill at the park across the street one evening.There were no bad surprises. Beautiful views out back as well.
Stayed 4 nights in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place to stay

This is a beautiful condo in a great location! I can't wait to book it again.
Stayed 2 nights in Jun 2019
From a partner site

10/10 Excellent

Wonderful stay Great location

Very comfortable stay. We have stayed at Trailhead Lodges for the past 4 years. Great location and great accommodations. Spacious and comfortable. Scenic area and is adjacent to annual Jazz Fest location. Has a pool, hot tub, and club house. Great place to stay!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Location

Everything you need and very walkable
Stayed 4 nights in Feb 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay

Property was very clean and the host was very responsive to any questions! The location was great and close to the ski resort. We had a great time at Winter Park and will definitely come back again! Thanks for hosting us.
Stayed 4 nights in Mar 2023
Verified review

10/10 Excellent

Favorite VRBO ever

This condo is perfect in every aspect. Perfect location, super clean, very roomy and the most beautiful view off the balcony. We will stay at this condo every single time we visit winter park.
Stayed 4 nights in Mar 2019
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent Location & Clean Property

We really enjoyed this condo. It has been one of our favorite properties to stay at in Winter Park. The location can't be beat, as you are in walking distance from everything in downtown WP. There is a park close by for the kids and the pool and hot tub at the property are very well maintained. We will definitely stay here again.
Stayed 3 nights in Mar 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Spacious and Serene

This was the perfect spot to stay with our family of 6. The patio overlooking the creek was my favorite spot. Being able to walk into town and the park made our stay even better. Our kids enjoyed the pool and hot tub. The rooms were very spacious and the beds were comfortable. Plenty of towels and other supplies. We have stayed at Trailhead many times and this is our new favorite condo.
Stayed 4 nights in Jul 2025
From a partner site

10/10 Excellent

Excellent

Everything was perfect. I love the communication - text and email and everything in between if you needed anything.
From a partner site

10/10 Excellent

Excellent

Very pleased with our stay. The condo was very clean, had every thing we needed in the kitchen, and the view was amazing. You can sit on the patio and listen to the nearby stream, rumble by. The instructions were clear and easy to follow. We didn't use the club facilities but they looked great. They even had a bike wash for our gravel bikes. Highly recommend this location.
Stayed 4 nights in Jul 2022
Verified review

6/10 Okay

Liked: Check-in, communication, location, listing accuracy
Disliked: Cleanliness
The unit was lovely however the dishes were not clean. The checkout process includes putting the dishes in the dishwasher and running the dishes. However, the housekeeping staff should check to make sure that the dishes that were run were clean before putting them away. Every plate have food still left on it. The fork, spoons and knives were not cleaned appropriately. The glasses and cups had stains in them so each item had to be re-washed before we can utilize them. Even the pots and pans had residual food left in them.In the master bathroom, the towels were dirty. Originally, I thought they were stains on the towel so I threw them in the wash to wash them and know they were not clean. so housekeeping should remove all tiles whether they look used or not, and wash them prior to the next guest arriving. I have stayed at multiple trailhead Lodge units over the last 15 years and this is the first time that I had experienced a cleanliness issue.
Stayed 3 nights in Jul 2026
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location close to wineries, breweries, and Lift Line stop to slopes

Great location, first stop on bus line to lifts, so you are sure to get a seat on way up to WP ski resort. The property manager answered all my texts quickly! was a great location and very nice property. Only seems to be a little short on kitchen supplies. For example, we wanted an 8x8 baking pan to bake brownies, but did not find one. Otherwise, a great experience!
Stayed 5 nights in Mar 2023
From a partner site

10/10 Excellent

Outstanding!

Wrapping up a couple of days here in the middle of an epic snow season! We've stayed @ Trailhead several times, and this trip was smooth as silk. Easy to find, easy parking, and we can walk to Deno's for pizza and around the cute downtown area. The kids love the bunk room, and it's far enough away from the master that we are able to sleep in a little. 424 had everything that we needed, and Winter Park Lodging always does an awesome job- I've stayed with them many times and they are my go to when I come to Winter Park. Highly recommend.
From a partner site

10/10 Excellent

4th of July in Winter Park!

We loved this condo! It was well-equipped and clean. The location of the property was super convenient to the park, shops and restaurants, but because this condo faced out to the mountains, we also had a beautiful view, peace and quiet. We used the pool and hot tub also. The only quibble I have is that there were not lamps on both sides of the bed in the Main bedroom, and no reading lamps in the family room. Over all, 5 stars! We will stay here again!
Stayed 4 nights in Jul 2022
From a partner site

2/10 Terrible

Definitely skip WP Seo Monday through Friday if you value peace and quiet

From 7:35 AM until 7:40 PM you will hear the consistent very loud beeping of the crane that moves construction workers inch by inch foot by foot floor by floor along the condo going up in the next complex. You will not hear the birds or the rushing of the river. You will not be able to shut all the windows turn on all the fans and blast YouTube nature videos to drowned out the beep beep beep beep. No one will tell you when you rent that this is what you paid for. We've been coming here for eight years. I don't think we will come back. Sadly, my husband drove me up here for a few days of rest. He is back in Denver with the car so I am stuck in the non-nature restful location promised
From a partner site

10/10 Excellent

Amazing condo

The location was beautiful, overlooking the woods and mountains. A short walk to downtown Winter Park. The condo was beautiful and cozy. The team was very attentive, accommodating, and understanding. Thank you for helping to make an amazing family vacation!
From a partner site

10/10 Excellent

Excellent

Nice place