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

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Welcome home to Trailhead Lodges 424
Trailhead Lodges pool & hot tub
Amazing mountain views off the patio.
Large couch with views & flat screen TV
Plush living room with Queen sofa pullout

Reviews

9.4 out of 10
Exceptional
2 bedrooms2 bathroomsSleeps 71188 sq ft

Popular amenities

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

Explore the area

View in a map
Winter Park, CO
  • Place, Hideaway Park
    ‪1 min walk‬
  • Place, Winter Park Visitor Center
    ‪3 min walk‬
  • Place, Bella Vita
    ‪5 min walk‬

Rooms & beds

2 bedrooms (sleeps 7)

Bunk Room

1 Single Bunk Bed and 1 Single Bed

Primary King Suite

1 King Bed

2 bathrooms

Primary Ensuite Bathroom

Bathtub · Toilet · Shower only

Shared Bathroom

Toilet · Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Separate dining area
Dining area

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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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock

About the area

Winter Park

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. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Winter Park, CO

What's nearby

  • Hideaway Park - 1 min walk - 0.1 km
  • Winter Park Visitor Center - 3 min walk - 0.3 km
  • Bella Vita - 5 min walk - 0.5 km
  • Blue Sky Massage - 7 min walk - 0.6 km
  • Grand Park Community Recreation Center - 16 min walk - 1.4 km

Getting around

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

Restaurants

  • ‪Wake N’ Bacon - ‬12 min walk
  • ‪The Noble Buck - ‬10 min walk
  • ‪McDonald's - ‬5 min walk
  • ‪Wendy's - ‬5 min drive
  • ‪Snoasis - ‬11 min drive

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 does it cost to stay at ☜ DOWNTOWN DIGS | Stay By The Park & Skiing | Trailhead Lodges 424 | Walk Everywhere?

As of 17 Mar, 2026, prices found for a 1-night stay for 2 adults at ☜ DOWNTOWN DIGS | Stay By The Park & Skiing | Trailhead Lodges 424 | Walk Everywhere on 16 May, 2026 start from S$318, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

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.

Reviews

9.4

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 40 out of 47 reviews
Rating 8 - Good. 4 out of 47 reviews
Rating 6 - Okay. 0 out of 47 reviews
Rating 4 - Poor. 1 out of 47 reviews
Rating 2 - Terrible. 2 out of 47 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Diane A.

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

10/10 Excellent

Bradley C.

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
This review is from a guest who booked and stayed through a partner site and can't be verified.

10/10 Excellent

Anna S.

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!
This review is from a guest who booked and stayed through a partner site and can't be verified.

10/10 Excellent

Norman S.

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

10/10 Excellent

Natalie G.

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
This review is from a guest who booked and stayed through a partner site and can't be verified.

10/10 Excellent

Douglas G.

Excellent

Great service and lodging. Only have good things to say.

10/10 Excellent

Matthew R.

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

Great Location

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

10/10 Excellent

Verified traveller

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
This review is from a guest who booked and stayed through a partner site and can't be verified.

10/10 Excellent

marc l.

Holiday season stay

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

10/10 Excellent

Keaton N.

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

10/10 Excellent

Shanna T.

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

10/10 Excellent

Melissa P.

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
This review was submitted before 2018 and can't be verified.

10/10 Excellent

David R.

Fantastic location + new building + great staff = great stay!

Great new property. Lots of sunlight. Close to the mountains. Very helpful staff.
Stayed 3 nights in Apr 2016
This review is from a guest who booked and stayed through a partner site and can't be verified.

10/10 Excellent

Linda M.

Excellent

Everything was perfect. I love the communication - text and email and everything in between if you needed anything.
This review is from a guest who booked and stayed through a partner site and can't be verified.

8/10 Good

Mike B.

Above Average

Very comfortable and clean thank you

10/10 Excellent

Bryan B.

Spacious Condo

Very clean spacious condo with all the amenities you would need. Great location, walking distance to restaurants and shops. Short drive or shuttle to slopes. I would definitely stay in this unit again when I come back to Winter Park.
Stayed 4 nights in Feb 2019
This review is from a guest who booked and stayed through a partner site and can't be verified.

10/10 Excellent

Joseph S.

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.
This review is from a guest who booked and stayed through a partner site and can't be verified.

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

8/10 Good

sharon l.

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
This review is from a guest who booked and stayed through a partner site and can't be verified.

10/10 Excellent

stacy c.

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.

8/10 Good

gini K.

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

spacious but not classy

The condo was spacious; the beds comfortable. It was nice to have open space outside the patio. However the artwork and decor was cheap and sterile. How many potpourri stuffed squirrels can one have? For the price of this condo, the furnishings were less than spectacular. The kitchen was sparsely stocked with odds and ends glasses and dishes, no dry measure measuring cups, no pasta strainer, and only two serving bowls.... Also, there was no grill on the AstroTurf patio. With a little effort on the part of the owners, this condo could be faublous.
Stayed 3 nights in Aug 2020
This review is from a guest who booked and stayed through a partner site and can't be verified.

2/10 Terrible

SUZIE T.

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

10/10 Excellent

Jason S.

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
This review is from a guest who booked and stayed through a partner site and can't be verified.

10/10 Excellent

Janessa H.

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!
This review is from a guest who booked and stayed through a partner site and can't be verified.

10/10 Excellent

Terri C.

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

About the host

Hosted by Winter Park Lodging Company

Host profile image
Winter Park Lodging Company provides custom, stress-free experiences for every type of traveler, offering high-end vacation homes, exceptional customer service, and sharing our passion for mountain living.

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 Aveda 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.

Guest will be required to sign a Winter Park Lodging Company rental agreement within 48 hours of booking.

Languages:

English

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