Condo - Rating 4.9 (47)

Trailhead 212 | Downtown, Pool & Hot Tub


Bedroom 1 bedrooms
Bathroom 1 baths
Guests 4 guests
Pets Not Allowed Pets Not Allowed

  • Address: 201 Trailhead Circle
  • Location: Winter Park
  • Type: Condo

Location Location

Description Description
Trailhead Lodges is conveniently located downtown Winter Park, just across from Hideaway Park which hosts world-class music festivals all summer long, including the Winter Park Jazz Festival and many more. This ground-level unit is located across from the clubhouse which features BBQ grills, a shared outdoor hot tub and heated swimming pool, and an expansive clubhouse with a pool table, kitchen, sitting area, workout room, and many more amenities. This unit also has a private patio, fully stocked kitchen, high-end appliances, and a gas fireplace.

County Permit 007422

Amenities:

Private Patio

Ground Level

Free High-Speed WiFI

Free Clubhouse Access

Shared outdoor Hot Tub

Shared outdoor heated swimming pool

Private washer and dryer

Gas fireplace

Cable TV

Smart lock for easy check In

Sleeping arrangements:

Primary bedroom – King Bed

Den – Pull out queen sofa

House Rules:

- No Pets

- No shoes are worn indoors

- No smoking of any kind in the home

- Quiet hours 10:00 pm till 7:00 am

-Parking for ONE car only

-Rv's and trailers are prohibited from parking at this site during holiday and music festival weekends.

Town of Winter Park Registration Number: 007422 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
Available
Unavailable
Check-In
Check-Out
August 2026
Su Mo Tu We Th Fr Sa
            1
2 3 4 5 6 7 8
9 10 11 12 13 14 15
16 17 18 19 20 21 22
23 24 25 26 27 28 29
30 31          
September 2026
Su Mo Tu We Th Fr Sa
    1 2 3 4 5
6 7 8 9 10 11 12
13 14 15 16 17 18 19
20 21 22 23 24 25 26
27 28 29 30      
October 2026
Su Mo Tu We Th Fr Sa
        1 2 3
4 5 6 7 8 9 10
11 12 13 14 15 16 17
18 19 20 21 22 23 24
25 26 27 28 29 30 31
November 2026
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 7
8 9 10 11 12 13 14
15 16 17 18 19 20 21
22 23 24 25 26 27 28
29 30          
December 2026
Su Mo Tu We Th Fr Sa
    1 2 3 4 5
6 7 8 9 10 11 12
13 14 15 16 17 18 19
20 21 22 23 24 25 26
27 28 29 30 31    
January 2027
Su Mo Tu We Th Fr Sa
          1 2
3 4 5 6 7 8 9
10 11 12 13 14 15 16
17 18 19 20 21 22 23
24 25 26 27 28 29 30
31            
February 2027
Su Mo Tu We Th Fr Sa
  1 2 3 4 5 6
7 8 9 10 11 12 13
14 15 16 17 18 19 20
21 22 23 24 25 26 27
28            
March 2027
Su Mo Tu We Th Fr Sa
  1 2 3 4 5 6
7 8 9 10 11 12 13
14 15 16 17 18 19 20
21 22 23 24 25 26 27
28 29 30 31      
April 2027
Su Mo Tu We Th Fr Sa
        1 2 3
4 5 6 7 8 9 10
11 12 13 14 15 16 17
18 19 20 21 22 23 24
25 26 27 28 29 30  
May 2027
Su Mo Tu We Th Fr Sa
            1
2 3 4 5 6 7 8
9 10 11 12 13 14 15
16 17 18 19 20 21 22
23 24 25 26 27 28 29
30 31          
June 2027
Su Mo Tu We Th Fr Sa
    1 2 3 4 5
6 7 8 9 10 11 12
13 14 15 16 17 18 19
20 21 22 23 24 25 26
27 28 29 30      
July 2027
Su Mo Tu We Th Fr Sa
        1 2 3
4 5 6 7 8 9 10
11 12 13 14 15 16 17
18 19 20 21 22 23 24
25 26 27 28 29 30 31
Swipe Swipe for Availability

Bedding Bedding
Room Beds Baths TVs Comments
Room 5 King

Amenities 41 Amenities
  • BBQ grill
  • Bed linen
  • Carbon monoxide alarm
  • Coffee maker
  • Cooking basics
  • Dedicated workspace
  • Dishes and silverware
  • Dishwasher
  • Dryer
  • Essentials
  • Extra pillows and blankets
  • Fire extinguisher
  • First aid kit
  • Free parking on premises
  • Freezer
  • Gym
  • Hair dryer
  • Hangers
  • Heating
  • Hot tub
  • Hot water
  • Hot water kettle
  • Indoor fireplace
  • Kitchen
  • Luggage drop-off allowed
  • Microwave
  • Oven
  • Patio or balcony
  • Pool
  • Pool table
  • Private entrance
  • Private living room
  • Refrigerator
  • Shampoo
  • Single level home
  • Smoke alarm
  • Stove
  • Toaster
  • TV
  • Washer
  • Wifi

Reviews Rating 4.9 (47) Reviews
Rating 5
This condo was very clean, had everything you’d
This condo was very clean, had everything you’d need and in a great location. We had trouble with the key pad but we were able to get ahold of the host right away and get a key. The kitchen was wonderful with nice pots and pans for cooking.
Cassena - Posted: 8/5/2026
Thanks for leaving a great review! Come back and visit!
Stay Vara staff
Rating 5
Great stay - would definitely stay again.
Great stay - would definitely stay again.
Kyler - Posted: 8/2/2026
Rating 5
Perfect place to stay for going to a music
Perfect place to stay for going to a music festival at Hideaway Park. Gated patio and quick access to trails was perfect for our dog.
Lawrin - Posted: 7/26/2026
thank you for sharing this! Sounds like it was the perfect home base for the festival at Hideaway Park, and we're so glad the gated patio and easy trail access worked out well for your pup too. Hope to host you again soon!
Stay Vara staff
Rating 5
Great location.
Great location.
Karen - Posted: 7/12/2026
Thank you for the wonderful review! We're delighted you enjoyed your stay. It was a pleasure hosting you, and we hope to welcome you back again soon!
Stay Vara staff
Rating 5
Loved it. We were close to everything but still
Loved it. We were close to everything but still felt like we were in a peaceful setting “off the beaten path”.
Stephen - Posted: 7/2/2026
Rating 5
Excellent place to stay! Loved the location, too!
Excellent place to stay! Loved the location, too!
Scott - Posted: 6/30/2026
Rating 5
Great place, great location. Enjoyed our time.
Great place, great location. Enjoyed our time.
Patrick - Posted: 3/30/2026
Thanks for the review!
Stay Vara staff
Rating 5
We always love staying here at Trailhead Lodge.
We always love staying here at Trailhead Lodge. It's a great location and the units are always beautiful. We feel right at home and look forward to our next visit! Thank you
Holly - Posted: 3/19/2026
Thank you for the great review!
Stay Vara staff
Rating 4
It was such a lovely stay!! The Airbnb was so
It was such a lovely stay!! The Airbnb was so close to everything we did a lot of walking around. The only small thing I would have to say is when I went to get water from the fridge there was a lot of little things in the water so probably haven’t changed the filter.
Adrianna - Posted: 2/23/2026
We are glad you enjoyed your stay. Thank you for the feedback on the water filter, we will check that asap. We hope to secure a 5 star review from you in the future and strive to address items as soon as we are told.
Stay Vara staff
Rating 5
Fantastic location! Everything in town is
Fantastic location! Everything in town is walkable from the unit - restaurants, trails, parks, you name it. It was clean and comfortable.
Hillary - Posted: 1/11/2026
Thanks Hillary! Glad the location made everything in town easy to walk to and that the unit was clean and comfortable. Hope to host you again in Winter Park.
Stay Vara staff
Rating 5
Great location. Very family friendly and walkable
Great location. Very family friendly and walkable to lots of fun activities. Management was wonderful with their communication. Would stay again.
Maria - Posted: 8/7/2025
Thanks for the review Maria! Come stay again soon!
Stay Vara staff
Rating 5
Great location for anything you want to do in
Great location for anything you want to do in Winter Park…..shopping, hiking, mountain biking, restaurants. Perfect location for dog owners, with green courtyard just outside the sliding doors. Conveniently located across from clubhouse and pool. Perfect for families. Decorated very cute with nod to Winter Park. Fireplace is a great touch. Contacted owner with a minor issue/request and it was handled within an hour!
Susan - Posted: 7/18/2025
Thank you very much Susan for the detailed review! Come back and see us again soon!
Stay Vara staff
Rating 5
Very nice space with a great location close to
Very nice space with a great location close to downtown Winter Park and a bus to the slopes. Fire place is a great touch. Only note is the walls are a bit thin so you can easily hear people walking up and down the hallway stairs from the bedroom.
Berkeley - Posted: 2/16/2025
Thanks for leaving a great review!
Stay Vara staff
Rating 5
Great location, great condo. Excellent
Great location, great condo. Excellent communication, and very responsive. Highly recommend!
Malai - Posted: 1/11/2025
Rating 4
Beds are not the comfiest (including the
Beds are not the comfiest (including the pullout). But the location is great for skiing, trails, and food. The space is nice and are very responsive.
Justice - Posted: 12/27/2024
Thanks for your feedback! We have contacted the owner about the beds! Thanks for staying with us.
Stay Vara staff
Rating 5
Great location, very clean and easy check in/out.
Great location, very clean and easy check in/out. Highly recommend.
Danielle - Posted: 8/21/2024
Thank you for the kind words Danielle. Come visit us again soon.
Stay Vara staff
Rating 5
We were able to walk everywhere during our stay -
We were able to walk everywhere during our stay - to the Brewfest, restaurants, hiking trails, and free bus to the ski area. Great weekend!
Kristine - Posted: 8/4/2024
It was such a pleasure hosting you guys! Glad you enjoyed your weekend here in WP!
Stay Vara staff
Rating 4
The rooms at Winter Park were clean and
The rooms at Winter Park were clean and comfortable, and had everything we needed for a few days stay. Sadly, we were very much looking forward to using the hot tub after our days of skiing, but it was inexplicably not in service.
Jean - Posted: 4/4/2024
Thanks for taking the time to leave a review Jean. Unfortunately we have no control over the hot tub since it is a community hot tub and managed by the HOA. We just manage the room specifically. We did offer to cover the cost of using the hot tub at the local rec center. Hope you have wonderful and safe travels on all your future adventures.
Stay Vara staff
Rating 5
This was the first host that has ever proactively
This was the first host that has ever proactively reached out to me to see if I needed anything. In fact, I did, but it was so small, I had forgotten to contact the host about it. So I mentioned this small thing to them in response to their question that they initiated, and immediately they had someone over to take care of the small thing. Great host. Great place to stay. Will stay with them again when we visit when I park. Well done and thank you Visit Winter Park!
Jason - Posted: 9/25/2023
Thanks for taking the time to write a review. We're delighted you enjoyed your stay, Jason. We hope you visit again soon.
Stay Vara staff
Rating 5
Great location for walking into downtown!
Great location for walking into downtown!
Ben - Posted: 9/5/2023
We're so glad you enjoyed your stay. Visit again soon!
Stay Vara staff
Rating 5
Great property. Nicely decorated and appointed!
Great property. Nicely decorated and appointed! Cleaning fee seems a bit excessive but otherwise no complaints
David - Posted: 8/24/2023
Rating 5
Great location, cozy accommodations, and great
Great location, cozy accommodations, and great communication!
Terry - Posted: 7/25/2023
Thanks Teresa, it was a pleasure to host you guys!
Stay Vara staff
Rating 5
Great location! Nice clean unit.
Great location! Nice clean unit.
Kim - Posted: 7/23/2023
Thanks Kim!
Stay Vara staff
Rating 5
Great unit. As described
Great unit. As described
Cheryl - Posted: 7/16/2023
Rating 5
Everything was great , right across the street
Everything was great , right across the street from the venue. Restaurants within close walking distance
Timothy - Posted: 7/8/2023
Rating 5
amazing stay!
amazing stay!
Savannah - Posted: 3/21/2023
Rating 5
Everything was great. Thank you.
Everything was great. Thank you.
Leif - Posted: 2/19/2023
Rating 5
Perfect for a weekend stay. Has everything you
Perfect for a weekend stay. Has everything you need and is close to everything as well.
Nitra - Posted: 10/2/2022
Rating 5
Great place all around!
Great place all around!
Phyllis - Posted: 9/4/2022
We are glad you enjoyed your stay Phyllis and thanks for taking the time to review the property! Cheers to all future adventures!
Stay Vara staff
Rating 5
Easy check-in, great location. The condo was well
Easy check-in, great location. The condo was well stocked with all necessary amenities. A cozy stay with easy access to hiking in and around Winter Park as well as about an hour from Rocky Mountain National Park.
Kimberly - Posted: 8/13/2022
Rating 5
Great property and location!
Great property and location!
Becca - Posted: 4/3/2022
Rating 5
Great place to stay. Clean and well located!
Great place to stay. Clean and well located!
Daniel - Posted: 3/23/2022
Thanks Daniel for taking the time to leave a great review! We are happy you enjoyed your stay & it was a pleasure hosting you all!
Stay Vara staff
Rating 5
This was a perfect place for us. The location was
This was a perfect place for us. The location was great too!!!
Sherri - Posted: 3/13/2022
Thanks Sherri for taking the time to review! It was a pleasure to host you guys and we are so glad you enjoyed the place and your time here in Winter Park!
Stay Vara staff
Rating 5
Amazing place with many amenities, will
Amazing place with many amenities, will definitely be going again!
Aleena - Posted: 2/6/2022
Rating 5
Great place. Heat is very comfortable and very
Great place. Heat is very comfortable and very convenient being on the first floor. Super close walk to downtown breweries/bars/restaurants. Nice fire place and very updated modern look. Club house was spot on with great amenities. In all would book again next ski trip!!
Emilio - Posted: 2/5/2022
Thanks Emilio! We enjoyed hosting you guys!
Stay Vara staff
Rating 5
Nicely appointed, and great location. The outdoor
Nicely appointed, and great location. The outdoor hot tub was an added bonus.
Leslie - Posted: 1/11/2022
Rating 5
Fantastic location and amenities! Super clean and
Fantastic location and amenities! Super clean and could walk to everything including the free shuttle to WPR. Perfect all around.
Victoria - Posted: 1/10/2022
Rating 5
So close to everything. Would stay again.
So close to everything. Would stay again.
Charles - Posted: 12/22/2021
Rating 5
This location is prime to being near everything!
This location is prime to being near everything! We loved walking to dinner and the park. The bed was so comfy! The club house was near by with a nice hot tub. They even included a lovely welcome package and teas! We were so impressed. Will absolutely stay here again. Loved it!
Rex - Posted: 9/21/2021
Thanks for a great review Rex! It was a pleasure to host you.
Stay Vara staff
Rating 5
Great place and location. 10am check out too
Great place and location. 10am check out too early.
Darren - Posted: 9/20/2021
Thank Darren! We have to do a 10am check out time due to cleaners and inspectors schedule. We want to make sure there is plenty of time for the property to turn over for the next guest! Thanks again for your feedback.
Stay Vara staff
Rating 5
Hosts were incredibly responsive. This place is
Hosts were incredibly responsive. This place is also close to everything in town.
Caran - Posted: 9/14/2021
Rating 5
Great place to stay in Winter Park! The unit
Great place to stay in Winter Park! The unit itself is cozy and clean and had everything you could need. The bed was very comfy and the my bedroom had more than enough space for our daughter to sleep in her pack n play. Access to the pool was also great. It’s also located really close to everything Winter Park had to offer. We would definitely stay here again if we were heading up to the mountains for a weekend!
Jade - Posted: 7/18/2021
Rating 4
The layout of the condo is suitable for 2 to 4
The layout of the condo is suitable for 2 to 4 adults and the pictures are actual. The master bed was comfortable. The private patio is gated and was convenient for us to use for storage of our bikes. Communication with rental company was excellent - we did have have an issue with noise overnight with the unit directly above us and it was addressed the next morning with the company. Something to be aware of is if you spend more time inside you may have to deal with foot step noise from the unit above along with noise from the hallway as there doesn’t seem to be much insulation to muffle it.
Cindy - Posted: 7/11/2021
Rating 5
Gorgeous little unit. We walked to downtown and
Gorgeous little unit. We walked to downtown and the sled hill. We cooked and did laundry. The place has everything you need! Perfect spot and it’s perfectly appointed.
Rand - Posted: 3/28/2021
Rating 5
We had an awesome time and we will definitely be
We had an awesome time and we will definitely be back again!
Virginia - Posted: 3/24/2021
Rating 5
Great bang for your buck! Great location!
Great bang for your buck! Great location!
Ryan - Posted: 3/16/2021
Rating 5
We were pleasantly surprised because we planned
We were pleasantly surprised because we planned this trip in 4 days and didn't do much research. This property was in a great location with access to restaurants, sporting shops and the center of town. The condo was spotless and included clear directions for checking- in and out. The bed was very comfortable and everything was easy to locate within the condo. I highly recommend stay at this property if you are planning a visit to Winter Park.
Tasha - Posted: 2/23/2021
Swipe Swipe for More Reviews

Have a question? Customer Questions & Answers Have a question? Customer Questions & Answers

Want to know specifics? Ask anything about this specific property that you would like to know...

Example: "Is the balcony screened in?" or "Is there a toaster oven?"


Request More Info Request More Info

Want to know specifics? Ask anything in reference to vacationing at this property that you would like to know...

Example: "Are fresh linens provided?"

I agree