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The Trailhead | Beautifully Furnished Modern Condo In Downtown Winter Park

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A wooden building with a covered patio area featuring outdoor seating, a fire pit, and a grill. - The Trailhead | Beautifully Furnished Modern Condo In Downtown Winter Park (Winter Park)
A modern kitchen with wooden cabinets, a black refrigerator, a granite countertop, and a bar area with leather stools. - The Trailhead | Beautifully Furnished Modern Condo In Downtown Winter Park (Winter Park)
A pool area with lounge chairs and a wooden building structure. - The Trailhead | Beautifully Furnished Modern Condo In Downtown Winter Park (Winter Park)
A modern kitchen with a central island, wooden cabinets, and a built-in oven. - The Trailhead | Beautifully Furnished Modern Condo In Downtown Winter Park (Winter Park)
A modern building with a curved roof, surrounded by a grassy area and trees. - The Trailhead | Beautifully Furnished Modern Condo In Downtown Winter Park (Winter Park)
Take advantage of a firepit, laundry facilities and a gym at The Trailhead | Beautifully Furnished Modern Condo In Downtown Winter Park. For some rest and relaxation, visit the hot tub. Guests can connect to free in-room WiFi.

Reviews

10 out of 10
Exceptional

Popular amenities

  • Pool
  • Spa pool
  • Kitchen
  • Washing machine
  • Dryer

Add dates for prices

About this property

The Trailhead | Beautifully Furnished Modern Condo In Downtown Winter Park

  • In floor radiant heat, fireplace. Three comfortable beds to sleep 6 people. We also supply a Pack and Play cot and High chair.

    Our condo is a modern mountain retreat. Modern art in all rooms. High definition Tv's in each room for your enjoyment.

    Guests have use of the entire apartment, along with clubhouse pool table and fitness room. Year round heated swimming pool and spa pool also available for guest use.

    Roger@innisfreehotels.com
    Cell 850-393-0063

    Within walking distance to all restaurants, night life, shopping, off-licence and supermarket..
    Hideaway Park is right next door and has incredible concert venues almost every weekend throughout the summer season. Sledding in the winter time.
    The best restaurants are;
    Deno's for Steaks and American food (one block on the left).
    The Ditch for Burritos and Awesome Hamburgers (one block on the left).
    Hernando's for Pizza and Italian food (four blocks to the right on the high street).
    Azteca for Mexican food (six blocks to the right on the high street).

    Ski area bus runs every 15 minutes to and from the ski area and is located one block from us.

    We are located one block from shopping, dining and nightlife. Directly across the street from Hideaway Park where summer concerts take place and sledding in the winter.
    There is a $45.00 one time pet fee. There is no smoking allowed in the condo but smoking is allowed on the balcony.

Similar properties

About the area

Winter Park is home to this apartment. Winter Park Ski Resort and Ski Granby Ranch are worth checking out if an activity is on the agenda. Amaze'n Maze Winter Park and Alpine Slide are also worth visiting. Visit our Winter Park travel guide
View more Apartments 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
  • Blue Sky Massage
    7 min walk - 0.6 km
  • Grand Park Community Recreation Center
    18 min walk - 1.5 km
  • Cozens Ranch House Museum
    2 min drive - 2.2 km

Getting around

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

Restaurants

  • McDonald's
    4 min walk
  • Sharky's
    5 min drive
  • Wendy's
    5 min drive
  • The Smokehouse BBQ
    6 min walk
  • Wake N’ Bacon
    12 min walk

Frequently asked questions

Does The Trailhead | Beautifully Furnished Modern Condo In Downtown Winter Park have a pool?

Yes, this property has a pool. Pool types include heated pools.

Is The Trailhead | Beautifully Furnished Modern Condo In Downtown Winter Park pet-friendly?

Yes, this property allows dogs (limit 2 total) with a maximum weight of up to 453 kg per pet.

How much is parking at The Trailhead | Beautifully Furnished Modern Condo In Downtown Winter Park?

On-site parking is available at the property.

What time is check-in at The Trailhead | Beautifully Furnished Modern Condo In Downtown Winter Park?

Check-in begins at 4:00 PM.

What time is check-out at The Trailhead | Beautifully Furnished Modern Condo In Downtown Winter Park?

Checkout is at 10:00 AM.

Where is The Trailhead | Beautifully Furnished Modern Condo In Downtown Winter Park located?

Situated in Winter Park, this apartment building is steps away from Hideaway Park and Winter Park Visitor Center. Bella Vita and Blue Sky Massage are also within 10 minutes.

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Reviews

The Trailhead | Beautifully Furnished Modern Condo In Downtown Winter Park Reviews

10

Exceptional

10

Cleanliness

10

Location

10

Property conditions & facilities
Rating 10 - Excellent. 230 out of 242 reviews
Rating 8 - Good. 11 out of 242 reviews
Rating 6 - Okay. 1 out of 242 reviews
Rating 4 - Poor. 0 out of 242 reviews
Rating 2 - Terrible. 0 out of 242 reviews

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect stay! Comfy furnishings, wonderfully stocked kitchen and great location to downtown Winter Park.
Stayed 4 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location, comfortable, responsive host. Lots of beautiful hiking close by. The kitchen had all the supplies we needed. We really enjoyed our stay.
Stayed 2 nights in Jun 2026
Verified review

10/10 Excellent

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

Great place

The place was a great place and great location
Stayed 3 nights in Apr 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Was perfect!! Fantastic location in the heart of Winter Park!! Pool and hot tub 50 feet away! Plus, bus stop was only a block away. Our host was excellent and very responsive!! Great Stay!!
Stayed 4 nights in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great set up for the 3 of us. Pool and hot top were right across the parking lot.
Stayed 3 nights in Mar 2026
Verified review

10/10 Excellent

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

Great family vacation

Location was wonderful, condo was spacious
Stayed 2 nights in Dec 2023
Verified review

10/10 Excellent

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

Spring skiing family getaway

Clean and cozy condo in a nice location!
Stayed 2 nights in Apr 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very clean , it was nice to have some spices, oil, vinegar on site . Thanks a lot !
Stayed 2 nights in Feb 2026
Verified review

10/10 Excellent

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

Perhaps getaway

We loved our stay at this property! Awesome location and beautiful condo. Would definitely stay here again!
Stayed 2 nights in Jul 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The condo at Trailhead is fantastic! The inside is exactly as pictured and very clean. The hot tub & heated pool are only steps away. It's right behind the park & very convenient to walk to bars & restaurants in the town. Highly recommend as a place to stay!
Stayed 4 nights in Aug 2025
Verified review

10/10 Excellent

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

Great spot

Stayed here with my friend and his 13 year old for a couple days of skiing. It's a great place and close to town/winter park shuttle. Nice hot tub and pool area as well. I would definitely stay here again.
Stayed 2 nights in Jan 2025
Verified review

10/10 Excellent

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

Excellent location

Excellent location for skiing and entertainment. Located right off of the main drive with plenty of parking. Outdoor hottub and heated pool were a bonus.
Stayed 4 nights in Jan 2025
Verified review

10/10 Excellent

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

Enjoyed our white Christmas

Excellent stay at an excellent condo! Just what we wanted and it was well-stocked with all the amenities. Exactly as promised. Great place to stay! would stay again!
Stayed 4 nights in Dec 2024
Verified review

10/10 Excellent

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

Jazz Fest

We loved the property, especially the location. The property owner was great to deal with.
Stayed 3 nights in Jul 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very clean home. Host was great. The kitchen was very well equipped and I appreciated the full size washer and dryer that were in the condo.
Stayed 3 nights in Oct 2025
Verified review

10/10 Excellent

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

Mountain hike

Great location right in town. Walk to many restaurants and stores. Easy drive to several trail heads. Great place
Stayed 3 nights in Oct 2024
Verified review

10/10 Excellent

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

Great

Location is perfect and Roger is a wonderful host!
Stayed 1 night in Aug 2024
Verified review

10/10 Excellent

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

Well stocked and great location

Loved the heated floors and clubhouse. This home was well stocked with spices and condiments, soft sheets and games.
Stayed 3 nights in Nov 2024
Verified review

10/10 Excellent

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

Great place

Great location. Very clean. We really appreciated the communication with the owner.
Stayed 4 nights in Jul 2024
Verified review

10/10 Excellent

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

Great place

Very well organized with everything you can possible need. Quick to respond on questions and provide immediate solutions. Wonderful place to stay in a great location.
Stayed 15 nights in Mar 2024
Verified review

10/10 Excellent

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

Race Weekend Getaway

We travel all over the mountains for ski races and stay in many different types of lodging. This location was wonderful, easy to access and the amenities were wonderful. We will for sure join you again!
Stayed 2 nights in Mar 2025
Verified review

10/10 Excellent

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

Great place close to town

Loved the balcony and bbq. Very close to town. Clean and very comfortable. Great pillows.
Stayed 2 nights in May 2024
Verified review

10/10 Excellent

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

Cool Summer week

We enjoyed this condo, location was ideal. Amenities were great, all the comforts we wanted. So many polite guests made our vacation special.
Stayed 11 nights in Jul 2023
Verified review

10/10 Excellent

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

Welcoming and perfect

We loved this place. We had everything we needed for our family of 4. The vibe was very welcoming, plenty of extras in the kitchen. Free coffee was great too!
Stayed 2 nights in Dec 2024
Verified review

10/10 Excellent

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

Wonderful condo

Great condo, Will absolutely rent again. Roger was very easy to communicate with as well! Clean, in a great location and perfect for a family of 4.
Stayed 1 night in Jan 2025