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

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A riverside park with a pond, picnic tables, and a red-roofed building with outdoor seating.
A lodge with multiple buildings, outdoor seating, and a mountain backdrop.
A living room with a stone fireplace, large windows, and a red ottoman.
An outdoor patio with a fire pit, barbecue grills, and outdoor seating.
A park with red swings and a fenced area.

Reviews

9.4 out of 10
Exceptional

Entire condo

2 bedrooms2 bathroomsSleeps 71188 sq ft

Popular amenities

  • Hot tub
  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • 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

Room options

About the neighborhood

Winter Park

This condo places you next to Hideaway Park and Winter Park Visitor Center. The condo includes a kitchen, a fireplace, and a balcony.
View more Condo Rentals in Winter ParkOpens in a new window

What's nearby

  • Hideaway Park - 1 min walk - 0.1 miles
  • Winter Park Visitor Center - 3 min walk - 0.2 miles
  • Bella Vita - 5 min walk - 0.3 miles
  • Blue Sky Massage - 7 min walk - 0.4 miles
  • Grand Park Community Recreation Center - 18 min walk - 1.0 mile

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
  • ‪Snoasis - ‬11 min drive

About this property

Entire place

You'll have the entire condo to yourself and will only share it with other guests in your party.

☜ 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.
The condo is heated and features a kitchen, 2 bathrooms, and a balcony. There's space to spread out with 2 bedrooms and a dining area. Guests can expect to find free WiFi and a Smart TV with a DVD player. Other standard amenities include a washing machine, a fireplace, and a coffee maker.

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  • Washer
  • Dryer
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Stunning townhome. Few minutes from Winter Park Ski Resort and Town of WP

Property amenities

Ski

  • Cross-country skiing nearby
  • Snowboarding nearby

Pool/Spa

  • Communal pool
  • Heated pool
  • Hot tub

Internet

  • Available in the condo: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Microwave
  • Oven
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Bathtub
  • Hair dryer
  • Shower
  • Towels provided

Living spaces

  • Dining table
  • Fireplace
  • Living room
  • Separate dining area

Entertainment

  • DVD player
  • Smart TV with cable/satellite channels

Outdoor areas

  • Balcony
  • Barbecue grill

Laundry

  • Laundry detergent
  • Laundry facilities
  • Washing machine

Comfort

  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Elevator
  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • In a village
  • In the city center
  • In the mountains
  • Near a hospital
  • Near an outlet shopping mall

Things to do

  • Arcade/game room
  • Billiards/pool table
  • Gym
  • Heated pool
  • Birdwatching nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Horseback riding nearby
  • Hunting nearby
  • Ice skating nearby
  • Kayaking nearby
  • Mountain biking nearby
  • Mountain climbing nearby
  • Rafting nearby
  • Rock climbing nearby
  • Sledding nearby
  • Snowmobiling nearby
  • Swimming nearby
  • Wildlife walks nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher
  • Deadbolt lock

General

  • Property located in a resort
  • Unit size: 1,188 square feet

Policies

Check-in

Check-in time starts at 4:00 PM

Contactless check-in available

Minimum check-in age: 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Information provided by the property may be translated using automated translation tools

Pets

  • This property doesn't allow pets

Children and extra beds

Children allowed: ages 0-17

Events

No events allowed

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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadbolt lock
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
  • Check-in: 4:00 PM
  • Check-out: 10:00 AM
  • Minimum check-in age: 25

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a carbon monoxide detector, a fire extinguisher, a smoke detector, and a deadbolt lock.

Property is also known as

Stay By The Park Look Out At Nature Awesome Amenities On Site

40814

Frequently asked questions

What's there to see around this condo?

This condo is located in Winter Park, just steps from Hideaway Park and Bella Vita, and within a short walk of Blue Sky Massage. You'll also find Winter Park Ski Resort and Colorado Adventure Park within a short drive.

Is there parking available at ☜ DOWNTOWN DIGS | Stay By The Park & Skiing | Trailhead Lodges 424 | Walk Everywhere?

No, there isn't parking available at the condo.

Is this condo next to a casino?

No, this condo is not connected to a casino.

Is there an indoor pool at this condo?

No, this condo doesn't have an indoor pool; however, there is a hot tub.

What will couples enjoy most about a stay at ☜ DOWNTOWN DIGS | Stay By The Park & Skiing | Trailhead Lodges 424 | Walk Everywhere?

Amenities that appeal to couples at this condo include a fireplace, a smart TV, and a kitchen.

Does ☜ DOWNTOWN DIGS | Stay By The Park & Skiing | Trailhead Lodges 424 | Walk Everywhere have a hot tub?

No, but this condo does have a heated pool.

Does this condo provide breakfast?

No, this condo doesn't offer breakfast.

Does this condo allow pets to stay for free?

No, pets aren't allowed at this condo.

Does ☜ DOWNTOWN DIGS | Stay By The Park & Skiing | Trailhead Lodges 424 | Walk Everywhere have connecting rooms available?

No, this condo doesn't feature connecting guestrooms.

Are there rooms with balconies at ☜ DOWNTOWN DIGS | Stay By The Park & Skiing | Trailhead Lodges 424 | Walk Everywhere?

Yes, every condo at ☜ DOWNTOWN DIGS | Stay By The Park & Skiing | Trailhead Lodges 424 | Walk Everywhere comes with a balcony and some offer mountain views.

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

Reviews

9.4

Exceptional

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

9.6/10

Cleanliness

Reviews

Verified review

10/10 Excellent

Nicholas J.

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

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
Verified review

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
Verified review

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
Verified review

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
From a partner site

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!
From a partner site

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
Verified review

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
From a partner site

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.
From a partner site

10/10 Excellent

Douglas G.

Excellent

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

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
Verified review

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
Verified review

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
Verified review

10/10 Excellent

Verified traveler

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

8/10 Good

Mike B.

Above Average

Very comfortable and clean thank you
From a partner site

10/10 Excellent

Linda M.

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

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.
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

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
From a partner site

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.
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

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
From a partner site

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!
From a partner site

10/10 Excellent

Chris B.

Excellent

Nice place
Verified review

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

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