Condo - Rating 4.7 (34)

Trailhead 812 Pet Friendly Downtown Winter Park


Bedroom 2 bedrooms
Bathroom 2 baths
Guests 7 guests
Pets Allowed Pets Allowed

  • Address: 801 Trailhead Circle
  • Location: Winter Park
  • Type: Condo

Location Location

Description Description
Trailhead Lodges – Downtown Winter Park Condo with Hot Tub, Pool & Event Access

Welcome to Trailhead Lodges, a stylish two-bedroom, two-bath condo located in the heart of downtown Winter Park. Perfect for families, couples, or groups, this ground-level unit offers convenient access to Hideaway Park and the Rendezvous event stage, home to world-class summer music festivals, including the Winter Park Jazz Festival. Relax after a day of skiing, hiking, or walking home from live events in a space designed for comfort and convenience.

Why You’ll Love It

Sleeps up to 7 guests with a King bedroom and bunk room with trundle

Ground-level condo with two private patios for relaxing outdoors

Gas fireplace and cozy living area for après-ski or evening downtime

Access to clubhouse amenities including BBQ grills, communal hot tub, heated pool, pool table, workout room, and sitting areas (please note the HOA manages the clubhouse not us)

Fully equipped kitchen for family meals or casual cooking

Inside the Home

This condo features a large primary suite with a King bed and oversized soaking tub, plus a second bedroom with a queen-over-queen bunk bed and trundle, ideal for families or friends. The open living area includes a gas fireplace, cable TV, and a soundbar for entertainment. Step outside to your two patios and enjoy mountain air while relaxing or dining al fresco.

Sleeping Arrangements

Primary Bedroom – King bed, en suite bath with oversized soaking tub

Second Bedroom – Queen-over-Queen bunk bed with pull-out trundle (lower bunk has limited clearance and is best suited for children).

Amenities Include

Free Wi-Fi

Cable TV + soundbar

Gas fireplace

Private washer & dryer

Two patios with outdoor seating

Smart lock for easy check-in

Ground-level access

Clubhouse access with pool table, kitchen, sitting area, workout room

Communal outdoor hot tub & heated swimming pool

Location Highlights

Steps from Hideaway Park & Rendezvous event stage

Downtown Winter Park restaurants, shops, and festivals within walking distance

Skiing and hiking trails nearby

Easy access to summer music festivals and community events

Good to Know

Town of Winter Park Registration Number: 005888

Pets allowed: Two medium dogs with $100 fee

No smoking in the condo

No shoes indoors

Quiet hours: 10 PM – 7 AM

Parking: Two cars only; RVs and trailers prohibited during holiday and festival weekends

The HOA manages the clubhouse, pool or hot tub - please note we are not in control of open/closing of these items. Visit Winter Park Lodging is locally owned and operated. We live in the community full time and enjoy playing and working in our wonderful mountain community. We would be honored for you to stay in one of our vacation homes on your next visit to Winter Park and the surrounding areas.

Please remember you’re staying in a home, not a hotel. Please treat the space with respect. If any problems arise, we will do our best to take action ASAP, but there is no one living on-site 24/7.


Availability Calendar Availability Calendar
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Swipe Swipe for Availability

Bedding Bedding
Room Beds Baths TVs Comments
Room 5 Bunk
Room 5 Single
Room 6 King

Amenities 50 Amenities
  • Baking sheet
  • Bathtub
  • BBQ grill
  • Bed linen
  • Blender
  • Body soap
  • Carbon monoxide alarm
  • Ceiling fan
  • Coffee maker
  • Conditioner
  • Cooking basics
  • Dedicated workspace
  • Dining table
  • Dishes and silverware
  • Dishwasher
  • Dryer
  • Essentials
  • Extra pillows and blankets
  • Fire extinguisher
  • First aid kit
  • Free on-street parking
  • Free parking on premises
  • Freezer
  • Gym
  • Hair dryer
  • Hangers
  • Heating
  • Hot tub
  • Hot water
  • Hot water kettle
  • Indoor fireplace
  • Kitchen
  • Microwave
  • Oven
  • Patio or balcony
  • Pool
  • Pool table
  • Private entrance
  • Private living room
  • Refrigerator
  • Shampoo
  • Shower gel
  • Single level home
  • Smoke alarm
  • Stove
  • Toaster
  • TV
  • Washer
  • Wifi
  • Wine glasses

Reviews Rating 4.7 (34) Reviews
Rating 3
Nice location, but a very dated place, needs a
Nice location, but a very dated place, needs a decent amount of maintenance and a full top to bottom clean. Bedding, pillows and all kitchenware need to be replaced. Would stay in this location again but wouldn’t choose this building/facility unless the newer options were unavailable or significant updates are made.
Bradley - Posted: 7/13/2026
Thank you for the honest feedback, and we're glad you enjoyed the location! We'll be following up with the owner about refreshing the bedding, pillows, and kitchenware, along with a deeper clean and general maintenance. We take these details seriously and appreciate you flagging them specifically. Thanks for staying with us!
Stay Vara staff
Rating 4
We had a very good stay. The location is
We had a very good stay. The location is convenient and comfortable for families. The manager was very responsive.
Tony And Whitney - Posted: 7/8/2026
Rating 5
A very clean and comfortable place to stay! Host
A very clean and comfortable place to stay! Host is very nice and responsive. The little sledding hill close by is awesome! Within walking distance of restaurants and shopping!
Latricia - Posted: 4/2/2024
It was such a pleasure to host you Latricia! We would love to have you back anytime! Cheers!
Stay Vara staff
Rating 5
This condo was perfect for our family ski
This condo was perfect for our family ski vacation! We loved that we could bring our dog-she had a blast playing ball at the park across the street as well as enjoyed daily hikes on the Vasquez Creek Trail. We loved the close proximity to shops and restaurants and the ski shuttle! The hosts were very communicative and responsive. Unfortunately the hot tub was broken while we were there, but they reimbursed us to use the rec center. We would highly recommend this condo to anyone looking to maximize their ski experience.
Katie - Posted: 3/31/2024
Thanks Katie, for taking the time to leave a stellar review. We wish we had more control over hot tub stuff, but glad you guys were able to enjoy it at the rec center! Cheers!
Stay Vara staff
Rating 5
Great place, great location! Would definitely
Great place, great location! Would definitely stay again.
Meghan - Posted: 3/29/2024
Rating 5
The staff went above and beyond to help us when
The staff went above and beyond to help us when it snowed starting the night before checkout. We were worried about the drive over berthoud pass to Denver airport, we were able to checkout a little later than 10am.
Michelle - Posted: 3/3/2024
Rating 4
We enjoyed our stay at this condo complex. We
We enjoyed our stay at this condo complex. We appreciated being able to find dog-friendly accommodations close to the ski resort and shops/food. Everything was very tidy and clean, and the management company stopped by just as we were arriving to replenish basic supplies. The second bedroom would have been better with a double bed that was not part of an over-sized bunk arrangement. It worked for a weekend but probably would not have felt comfortable for a longer stay. Close to the free shuttle to the ski resort and to other condo complexes. For families, a perk would be a gentle tubing hill right in front of the complex, free, with tubes provided.
Ginna - Posted: 2/27/2024
Thanks Ginna for taking the time to review the property! It sounds like a 5 star review but wondering why you gave us 4 stars. We enjoyed hosting you all. Cheers to all your future adventures!
Stay Vara staff
Rating 5
This was a nice place. It was clean except the
This was a nice place. It was clean except the kitchen oven and some dishes, pots and pans that were put up in the cabinets dirty or full of grease. Oven was smoking so we figured out it wasn’t cleaned. I’m guess owners trusted a cleaning person to do the job correctly and the cleaning personnel didn’t do a good job. Either way my wife cleaned it and washed the pots etc and it was fine. We would stay here again
Daniel - Posted: 12/16/2023
Your wife is the best! Please thank her for us. We are following up with the cleaners to address your concerns. Thanks for staying and we look forward to having you again!
Stay Vara staff
Rating 5
A beautiful condo in the middle of town; great
A beautiful condo in the middle of town; great for kids being across the street from the skate park, playground and amphitheater/lawn.
Tim - Posted: 8/20/2023
Thanks for taking the time to leave a great review! We're so glad you enjoyed your stay.
Stay Vara staff
Rating 5
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N/A
Michele - Posted: 7/19/2023
Rating 5
The location was perfect and the condo was
The location was perfect and the condo was spacious and comfortable.
Sheryl - Posted: 6/26/2023
Rating 5
Great stay in Winter Park. Close to lots of shops
Great stay in Winter Park. Close to lots of shops and restaurants. Great little sledding hill just around the corner. Loved that we were able to bring our pups with us. Condo was clean, cozy, and had lots of great amenities.
Lindsay - Posted: 4/2/2023
We are so glad you and the whole family, even the pups, enjoyed your stay!
Stay Vara staff
Rating 5
Great location in winter park, close to downtown
Great location in winter park, close to downtown and the park and also awesome to have the sledding hill behind us and the pool across. Kids had plenty to do!! we stayed here as a family of four and also had other friends in the condo, so we had enough space to host dinners/ entertaining for 12 at a time with the openness of the lay out. Well stocked, good and responsive property manager.
Heidi - Posted: 3/24/2023
Rating 4
Nice place. Only a few things that needed work.
Nice place. Only a few things that needed work. One, we had to wait 30 minutes past check in time before we were able to get in. Was told I’d be notified when it was ready, decided to text after 30 minutes past and received a “Oh sorry, yes it was ready at 4pm”. Also, there was duct tape wrapped around the kitchen sink faucet. Not what you want to see when you pay so much. Other than those minor issues it was a nice apartment and located conveniently to amenities. I would recommend.
Erin - Posted: 3/17/2023
Thanks for taking the time to review, we appreciate the feedback! This unit was a check out the day of your arrival and we were not able to get it ready prior to 4 so we didn't text. Also, the kitchen faucet was leaking, and the quick fix was tape. The day of your check out we installed a brand-new kitchen faucet! We hope to have you back in the future.
Stay Vara staff
Rating 4
The Trailhead offers everything our family needed
The Trailhead offers everything our family needed to stay for a long weekend in Winter Park. We walked to restaurants (Rollin’ was a fav for breakfast), and also used the hot tub and grill closer to home. The condo was very quiet, which made it easy to enjoy our time together!
Kimmie - Posted: 2/8/2023
Rating 5
Great place!!
Great place!!
Jennifer - Posted: 1/16/2023
Rating 5
Really enjoyed this condo. Nice size. Well
Really enjoyed this condo. Nice size. Well equipped. Clean. Very responsive management.
Liz - Posted: 8/17/2022
Thanks Liz for taking the time to review the property! We enjoyed hosting you!
Stay Vara staff
Rating 5
We had a wonderful stay at this condo with our 2
We had a wonderful stay at this condo with our 2 dogs and only wish we could stay a little longer. The host was very good with communicating with us. The condo was very clean, well stocked, very spacious and had a wonderful layout. The location was awesome: there were 2 parks nearby and a walking distance to many restaurants. We were able to enjoy a free concert at the park right next door! We will try to be back soon!
Anya - Posted: 8/14/2022
We are so glad you enjoyed your stay! The location of these condos are perfect with everything around! It was a pleasure to host you guys, please come back and visit! Thanks for leaving a great review!
Stay Vara staff
Rating 5
This was our first visit to Colorado and it
This was our first visit to Colorado and it exceeded our expectations. We loved this place! It was a great location with pool and hot tub. Walking distance to great restaurants and shops. Close to numerous trails. The condo was super clean and had everything you would need. We highly recommend this place and will be back in the future!
Jennie - Posted: 8/12/2022
Thank Jennie! We enjoyed hosting you guys and we are so glad you enjoyed your stay :)
Stay Vara staff
Rating 5
Amazing location, huge 2br condo. Super family
Amazing location, huge 2br condo. Super family friendly and you can walk just about anywhere in WP. We used the community grills and pool and had a blast!
Julie - Posted: 7/6/2022
Thanks for leaving a great review Julie! We enjoyed hosting you guys! You and your family are welcome back anytime!
Stay Vara staff
Rating 5
We love Winter Park!
We love Winter Park!
Tom - Posted: 6/27/2022
Thanks Tom!
Stay Vara staff
Rating 5
We had a great time and everything was very nice.
We had a great time and everything was very nice.
Edgar - Posted: 6/6/2022
Rating 4
Amazing location- sledding and walking trails at
Amazing location- sledding and walking trails at Hideaway Park. Walking distance to ski shuttle and dinner spots.
Rebecca - Posted: 3/6/2022
Rating 5
Cozy and spacious condo located in the heart of
Cozy and spacious condo located in the heart of Winter Park, central to shops and restaurants, and just a quick 10-minute drive to Winter Park Resort. Plenty of room for 2 adults, 2 kids and a dog. We loved the big kitchen, and comfy couches and fireplace. The kids loved the complex's heated pool and hot tub. Would recommend!
Jenner - Posted: 1/31/2022
We are so glad you enjoyed the property! It is definitely convenient and central to everything in town! Thanks for visiting and staying with us!
Stay Vara staff
Rating 4
Great location!
Great location!
David - Posted: 1/12/2022
Rating 5
This was one of the best places ive been so far
This was one of the best places ive been so far in winter park. The community area was really nice i enjoyed the hot tub every day. It is the furthest ive stayed from the lifts its a short drive or a decent bus ride to the gondola, but its right next to a park and close to shopping and restaurants in winter park. I think it was well worth the price and the staff was helpful and friendly throughout my stay.
Aimee - Posted: 1/2/2022
Wow! Thanks for the amazing review! We enjoyed hosting you guys! Come back and visit anytime!
Stay Vara staff
Rating 5
Great location, the condo is even larger and
Great location, the condo is even larger and nicer than the pictures. We had a wonderful family Thanksgiving and would stay here again for sure!
Julie - Posted: 11/26/2021
We are so glad you guys enjoyed your stay during the holidays! We would love to host you guys again, come visit again :)
Stay Vara staff
Rating 5
Really great spot and super clean. Space was
Really great spot and super clean. Space was bigger than it looked in the pictures. Ground level was also nice with easy access to the pool and hot tub. Would definitely stay again!
James - Posted: 10/18/2021
We are so glad you had a great weekend! Thanks for your great review. Come back anytime!
Stay Vara staff
Rating 5
Super clean and great location right in the heart
Super clean and great location right in the heart of Winter Park. Check-in was super easy as well.
Andrew - Posted: 10/16/2021
Thanks for the kind words Andrew! We are glad you enjoyed your stay :)
Stay Vara staff
Rating 5
Place was very close to restaurants and exactly
Place was very close to restaurants and exactly as described
Madeline - Posted: 10/3/2021
Rating 5
Really nice condo in a fantastic location close
Really nice condo in a fantastic location close to everything.
David - Posted: 7/23/2021
Rating 4
Nice place, nice location, comfortable for 3-4
Nice place, nice location, comfortable for 3-4 people but many minor issues that are easily fixed. Great job communicating and some nice touches inside but property had many minor issues and the carpet needs a cleaning. The microwave pad is broken- the number “2” does not work. The soap and shampoo dispenser in master bath did not work. The exceedingly cheap wine bottle opener is bent, the britta filter is expired, the electronic trash can did not work. The managing company was very responsive. The property is a solid four.
Stuart - Posted: 6/14/2021
Rating 5
One of the best places we have stayed in Winter
One of the best places we have stayed in Winter Park. We were happy we could bring the dogs with us & enjoy the walking paths nearby. The condo was perfect - including the living room setup, well equipped kitchen and radiant floor heating. The queen size bunk beds were a treat for the kids.
Lisa - Posted: 2/1/2021
Rating 5
This place is better than the pictures show!
This place is better than the pictures show! 100ft walk to sledding in the park/cross country ski. More spacious and beds if needed. Easy parking and great first level condo.
Andy - Posted: 1/19/2021
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