☜ 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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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. Enjoy the area's slopes with cross-country skiing and snowboarding, and don't miss out on the snowmobiling and sledging.
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 - 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
Snoasis - 11 min drive
The Noble Buck - 10 min walk
Wake N’ Bacon - 12 min walk
McDonald's - 5 min walk
The Smokehouse BBQ - 7 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 does it cost to stay at ☜ DOWNTOWN DIGS | Stay By The Park & Skiing | Trailhead Lodges 424 | Walk Everywhere?
As of 8 May 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 10 May 2026 start from AU$420, 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.
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.
While there was a slight issue, they resolved it quickly and the accommodations were excellent!
Bradley C.
Stayed 3 nights in Jan 2026
Response from VrboOwner on 23 Jan 2026
We are so happy we could resolve your small issue quickly! Thank you so much for staying with us.
From a partner site
10/10 Excellent
Anna S.
29 July 2025
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!
Anna S.
From a partner site
10/10 Excellent
Norman S.
18 Apr 2025
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
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.
Verified traveller
Stayed 4 nights in Jul 2025
Response from VrboOwner on 2 Aug 2025
Fantastic! We are so happy you found a new favorite condo at Trailhead Lodges. Thank you for sharing your comments and reach out for to us when you are planning another stay! We would love to host you again.
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.
Keaton N.
Stayed 4 nights in Mar 2023
Response from VrboOwner on 10 Mar 2023
Great to hear you loved Trailhead Lodges 424 Keaton! We appreciate your review and would love to welcome you back to the mountains again. Don't forget, we always give a return guest discount too!
~The Winter Park Lodging Company Team
Verified
10/10 Excellent
Shanna T.
15 Mar 2019
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.
Shanna T.
Stayed 4 nights in Mar 2019
Response from VrboOwner on 24 Mar 2020
Yay! That's so great to read. We are so pleased you enjoyed your stay with us. Please reach out again when you come back to enjoy the mountains.
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.
Melissa P.
Stayed 3 nights in Mar 2022
Response from VrboOwner on 18 May 2022
Melissa, we would love to welcome you back to Trailhead Lodge 424. Thank you for staying with us. It's great when you find a vacation spot you love! Give us a shout when you want to stay again. We always give a return guest discount.
~The Winter Park Lodging Company Team
Archival
10/10 Excellent
David R.
1 May 2016
Fantastic location + new building + great staff = great stay!
Great new property. Lots of sunlight. Close to the mountains. Very helpful staff.
David R.
Stayed 3 nights in Apr 2016
Response from VrboOwner on 24 July 2021
Thank you so much for the very nice review you posted of your stay with Winter Park Lodging Company. We appreciate you taking the time to write that up and submit it. We'd love to host you again!
From a partner site
10/10 Excellent
Linda M.
3 Oct 2024
Excellent
Everything was perfect. I love the communication - text and email and everything in between if you needed anything.
Linda M.
Verified
10/10 Excellent
Bryan B.
27 Feb 2019
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.
Bryan B.
Stayed 4 nights in Feb 2019
Response from VrboOwner on 24 Mar 2020
Thank you Bryan! We are so pleased you enjoyed your stay with us at Trailhead Lodges 424. Please call us when you're back this way again.
From a partner site
8/10 Good
Mike B.
27 Mar 2024
Above Average
Very comfortable and clean
thank you
Mike B.
From a partner site
10/10 Excellent
Joseph S.
4 Feb 2024
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.
Joseph S.
From a partner site
10/10 Excellent
26 July 2022
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.
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!
sharon l.
Stayed 5 nights in Mar 2023
Response from VrboOwner on 25 Mar 2023
Thank you so much Sharon for staying with us and for taking the time to write a review. We will definitely check the kitchen inventory and get needed items added! Brownies on vacation are a must!
~The Winter Park Lodging Company Team
From a partner site
10/10 Excellent
stacy c.
28 Jan 2023
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.
stacy c.
From a partner site
10/10 Excellent
8 July 2022
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!
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.
gini K.
Stayed 3 nights in Aug 2020
Response from VrboOwner on 23 July 2021
Thank you so much for the review you posted of your stay with Winter Park Lodging Company. We really appreciate you taking the time to write that up and submit it. We are sharing your feedback with the owner.
We'd love to host you again!
From a partner site
2/10 Terrible
SUZIE T.
13 July 2022
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
SUZIE T.
About the host
Hosted by Winter Park Lodging Company
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
Premier Host
They consistently provide great experiences for their guests