Perfectly placed in downtown Winter Park, Trailhead Lodges 811 is a cozy one bedroom condo that's just steps to Rendezvous Event Center, local shops & restaurants, and even a fun playground and skate park. Plus, this condo is pet-friendly, so bring your dog (one) to Winter Park to enjoy some mountain adventures!
Located on the first level of building 8, this home has easy access for everyone. Walk into the open living room & kitchen area and settle right in. The plush living room has updated furniture, a gas fireplace, walk-out patio, and open access to the kitchen & dining areas. Speaking of the kitchen, you'll love the full size kitchen with everything the chef in your group will need to whip up an easy at home dinner. Don't want to cook? You're just steps from some of the best drinks & dining in Winter Park.Ready to rest easy? Snuggle up in the Primary King bedroom with hotel-style linens that promise an excellent night's sleep. This condo also features a Queen pullout in the living room and a shared full bathroom with hallway access for everyone. Finally, make sure to take a dip in the pool & hot tub to relax your tired muscles after a fun day on the trails and slopes!Sleeping Arrangements: King Primary bedroom, plus a Queen-sized pullout sofa in the living area. Sleeps up to four guests.Local Deals: Save on local adventurous activities, gear rentals, transportation, and more when booking with us. Discount codes will be sent after booking.Please Note:
Pet Friendly: This home is pet friendly for one dog. There is a required $25 nightly fee for one dog which will be added to your reservation at time of checkout.
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.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: 017124
The Winter Park Lodging Company Difference
December 2024 | ||||||
---|---|---|---|---|---|---|
Sun | Mon | Tue | Wed | Thu | Fri | Sat |
01 | 02 | 03 | 04 | 05 | 06 | 07 |
08 | 09 | 10 | 11 | 12 | 13 | 14 |
15 | 16 | 17 | 18 | 19 | 20 | 21 |
22 | 23 | 24 | 25 | 26 | 27 | 28 |
29 | 30 | 31 |
January 2025 | ||||||
---|---|---|---|---|---|---|
Sun | Mon | Tue | Wed | Thu | Fri | Sat |
01 | 02 | 03 | 04 | |||
05 | 06 | 07 | 08 | 09 | 10 | 11 |
12 | 13 | 14 | 15 | 16 | 17 | 18 |
19 | 20 | 21 | 22 | 23 | 24 | 25 |
26 | 27 | 28 | 29 | 30 | 31 |
February 2025 | ||||||
---|---|---|---|---|---|---|
Sun | Mon | Tue | Wed | Thu | Fri | Sat |
01 | ||||||
02 | 03 | 04 | 05 | 06 | 07 | 08 |
09 | 10 | 11 | 12 | 13 | 14 | 15 |
16 | 17 | 18 | 19 | 20 | 21 | 22 |
23 | 24 | 25 | 26 | 27 | 28 |
March 2025 | ||||||
---|---|---|---|---|---|---|
Sun | Mon | Tue | Wed | Thu | Fri | Sat |
01 | ||||||
02 | 03 | 04 | 05 | 06 | 07 | 08 |
09 | 10 | 11 | 12 | 13 | 14 | 15 |
16 | 17 | 18 | 19 | 20 | 21 | 22 |
23 | 24 | 25 | 26 | 27 | 28 | 29 |
30 | 31 |
April 2025 | ||||||
---|---|---|---|---|---|---|
Sun | Mon | Tue | Wed | Thu | Fri | Sat |
01 | 02 | 03 | 04 | 05 | ||
06 | 07 | 08 | 09 | 10 | 11 | 12 |
13 | 14 | 15 | 16 | 17 | 18 | 19 |
20 | 21 | 22 | 23 | 24 | 25 | 26 |
27 | 28 | 29 | 30 |
May 2025 | ||||||
---|---|---|---|---|---|---|
Sun | Mon | Tue | Wed | Thu | Fri | Sat |
01 | 02 | 03 | ||||
04 | 05 | 06 | 07 | 08 | 09 | 10 |
11 | 12 | 13 | 14 | 15 | 16 | 17 |
18 | 19 | 20 | 21 | 22 | 23 | 24 |
25 | 26 | 27 | 28 | 29 | 30 | 31 |
June 2025 | ||||||
---|---|---|---|---|---|---|
Sun | Mon | Tue | Wed | Thu | Fri | Sat |
01 | 02 | 03 | 04 | 05 | 06 | 07 |
08 | 09 | 10 | 11 | 12 | 13 | 14 |
15 | 16 | 17 | 18 | 19 | 20 | 21 |
22 | 23 | 24 | 25 | 26 | 27 | 28 |
29 | 30 |
July 2025 | ||||||
---|---|---|---|---|---|---|
Sun | Mon | Tue | Wed | Thu | Fri | Sat |
01 | 02 | 03 | 04 | 05 | ||
06 | 07 | 08 | 09 | 10 | 11 | 12 |
13 | 14 | 15 | 16 | 17 | 18 | 19 |
20 | 21 | 22 | 23 | 24 | 25 | 26 |
27 | 28 | 29 | 30 | 31 |
August 2025 | ||||||
---|---|---|---|---|---|---|
Sun | Mon | Tue | Wed | Thu | Fri | Sat |
01 | 02 | |||||
03 | 04 | 05 | 06 | 07 | 08 | 09 |
10 | 11 | 12 | 13 | 14 | 15 | 16 |
17 | 18 | 19 | 20 | 21 | 22 | 23 |
24 | 25 | 26 | 27 | 28 | 29 | 30 |
31 |
September 2025 | ||||||
---|---|---|---|---|---|---|
Sun | Mon | Tue | Wed | Thu | Fri | Sat |
01 | 02 | 03 | 04 | 05 | 06 | |
07 | 08 | 09 | 10 | 11 | 12 | 13 |
14 | 15 | 16 | 17 | 18 | 19 | 20 |
21 | 22 | 23 | 24 | 25 | 26 | 27 |
28 | 29 | 30 |
October 2025 | ||||||
---|---|---|---|---|---|---|
Sun | Mon | Tue | Wed | Thu | Fri | Sat |
01 | 02 | 03 | 04 | |||
05 | 06 | 07 | 08 | 09 | 10 | 11 |
12 | 13 | 14 | 15 | 16 | 17 | 18 |
19 | 20 | 21 | 22 | 23 | 24 | 25 |
26 | 27 | 28 | 29 | 30 | 31 |
November 2025 | ||||||
---|---|---|---|---|---|---|
Sun | Mon | Tue | Wed | Thu | Fri | Sat |
01 | ||||||
02 | 03 | 04 | 05 | 06 | 07 | 08 |
09 | 10 | 11 | 12 | 13 | 14 | 15 |
16 | 17 | 18 | 19 | 20 | 21 | 22 |
23 | 24 | 25 | 26 | 27 | 28 | 29 |
30 |
Room | Beds | Baths | Comments |
---|---|---|---|
Primary King Bedroom | King | Shared Bathroom | Main Level |
Living Area | Sleep Sofa | Shared Bathroom | Main Level |
By Mike, Posted: 07/30/2024We had an outstanding stay at Trailhead Lodges 811. The unit is very nicely decorated and in perfect condition. The location in downtown Winter Park was ideal for us too. Thank you so much.
MANAGER'S COMMENTS: We are so happy you loved Trailhead Lodges 811 and found it in perfect condition! We hope you'll with us again!
~The Winter Park Lodging Company Team
By Julie, Posted: 04/25/2024Nice place, easy to book.
MANAGER COMMENTS: Thanks for letting us know Julie! It's great when you can take your dog along with you. Reach out when we can host you again! ~ The Winter Park Lodging Company Team
By Fae, Posted: 02/05/2024A terrific pet friendly spot to enjoy Winter Park! Always terrific/appreciate when we can bring our hound. Really nice size for a 1 bedroom condo and excellent location right in downtown. Just a quick walk to everything. We love Winter Park Lodging Company.....they're the best! Just a comfortable spot to stay and has all you need. We'll for sure be back folks and thanks again for everything. - Fae
MANAGER COMMENTS: Well thanks again Fae! Always a pleasure to host you and Storm. Looking forward to working you you again soon! ~ The Winter Park Lodging Company Team
By Ricardo, Posted: 07/11/2023Everything about this stay was perfect: the location, the communication from start to finish, the actual accommodations, the cleanliness. Our request for an early check-in was granted. The unit was extremely clean and had more than enough stocked for us to stay (spices, dishes, glasses-you name it, it was there). Parking was easy and there was a place for our bikes right on our porch. The instructions for entering and leaving upon departure were easy to understand. I can't think of a thing that could be improved. We will most certainly stay there again when we go to Winter Park. Thank you all.
MANAGER'S COMMENTS: We really appreciate this review and all of your positive comments Ricardo. We hope you will be able to stay with us again!
~The Winter Park Lodging Company Team
By Patricia, Posted: 06/09/2023We were so happy with the condo. It was just as pictured on the website. We even had a young moose come up to the trees near our door to eat some leaves. It is a wonderful property and we will be back.
MANAGER'S COMMENTS: Wildlife sightings are exciting and make for a special stay in the mountains! We are happy you loved Trailhead Lodges 811 Patricia. Thank you for taking the time to share your review. We look forward to hosting you again!
~The Winter Park Lodging Company Team
By Eddie, Posted: 01/23/2023Happy to be able to bring our dog! Had a blast snowshoeing and running on the Fraser Trail with him. Plenty of room for 2 folks....and a dog. Very easy to get everywhere from here. Thanks for your great hospitality!
MANAGER COMMENTS: Excellent...always better when the dog came come too! Please do reach out if your travels bring you back this way Eddie. ~ The Winter Park Lodging Company Team
By Rick, Posted: 09/19/2022We had a good visit. I was impressed with your handling of our reservation and the accommodations were just what we wanted and needed.
MANAGER COMMENTS: Many thanks for letting us know Rick. We do hope you'll join us again....in Winter Park or Steamboat Springs! ~ Winter Park Lodging Company Team
By Donald, Posted: 09/06/2021Trailhead Lodges were nicely furnished and very welcoming. We had a one bedroom ground floor which we appreciated not having to climb stairs. The welcome goodies were a nice touch. We felt at home the 4 night's that we were there. It was nice to be within walking distance of shopping and restaurants. The walking trail and park nearby are a nice plus to the area. I would recommend for summer or winter vacation.
MANAGER COMMENTS: Terrific! Thanks for letting us know Donald. It is handy being so close to walking to it all. Please do come stay again!
By Frank, Posted: 07/28/2021This was a totally hassle-free online check-in & check-out. No forms to fill out, no bored counter person asking a hundred inane questions, all done on my phone. I was truly amazed!
MANAGER COMMENTS: So pleased you guys enjoyed our check in/out process. We did try to make it as hassle-free as possible. Hope you'll join us again.
By FatKid, Posted: 03/30/2021I stayed at 811 Trailhead in late March. I can not say enough about the Trailhead complex. I have been in the larger multi bedroom units in the past and had no complaints. 811 is no different. Great rental with a full kitchen and huge bed. The living room is big. The pullout couch makes it great for more than 2 if the extras don't mind bunking up together. If there is any kind of negative it is being on the first floor in the morning. If your neighbors above decide to practice river dance or mixed martial arts you know they are there. BUT, that is any multi story complex anywhere. 1st floor for me is a plus because I have ski and board bags. WPLC to the front of the line!
MANAGER COMMENTS: Thanks for sharing your stay candidly. So pleased you found a great spot you continue to enjoy in Trailhead. Looking forward to working with you again!
By Jose, Posted: 07/29/2020The apartment was clean, organized, well decorated and cozy. Convenient parking and space for our bicycles.
MANAGER COMMENT: Looks like the Trailhead Lodges 811 checked all the boxes. Come see us for another visit soon.
By Valerie, Posted: 06/16/2020We had a wonderful getaway at the Trailhead property! It's very centrally located and a lot of restaurants and amenities were walkable. The large neighborhood park and the playground was a great bonus. The Unit was ready before we got to town and was very clean and also had a note and welcome gift for my husbands birthday which we were celebrating. Space was large enough for our family of four! We enjoyed the trails near by as well. Great location and relaxing getaway in Winter Park!
MANAGER COMMENT: Glad your hubby had a happy B-day! Every year is another year full of great memories. Come make more memories soon.
By Stan, Posted: 01/17/2020My wife and I enjoyed another wonderful week at Winter Park. The condo was very comfortable so we felt just like home. The only negative would be the quality of the bed. Apparently the mattress was worn out so the topper didn't really help. Other than that we were very satisfied with the quality and cleanliness.
MANAGER COMMENTS: Got it. We'll get figuring on how to get that mattress updated. We are so glad everything else worked out well. Thanks!
By Carl, Posted: 08/18/2019Nicely appointed and roomy 1 bed --1 bath condo. Just off Main Street in center of WP. Our accommodations were just right!! However, hot tub was not working.
Manager Comment: Apologies for the hot tub being down for part of your stay. The part has been replaced and the tub is up and running again. Come see us soon for a soak.
By Kim, Posted: 03/01/2019We had a great experience staying at Trailhead Lodge 811. It was a very comfortable and homey place with everything we could possibly need. The location was close to shopping and restaurants which was another plus! We will not hesitate to rent from Winter Park Lodging Company in the future. We’ve never been disappointed!
MANAGER COMMENTS: Many thanks Kim! We are so pleased you enjoyed your stay at Trailhead 811 this time and we're looking forward to seeing you next month again.
By Raelene, Posted: 02/06/2019Everything about our experience was excellent beginning with the reservation process to the check out. Winter Park Lodging Company was terrific. The website was easy to use, the photos were accurate, the communication from the time we booked until we checked out was great. On the day of our arrival, I received a text that the condo was available for early check in. Unfortunately, our flight didn't get in until later that evening. While we were waiting to pick up our rental car, I received a call to just check in and make sure everything was as we expected and to see if we needed anything. The condo itself is beautifully appointed and felt like home. The decor and furnishings are of good quality and the place was spotless. After we had left the condo on the last day, we realized we had left something there. I called the office and they were able to remotely unlock the door so we could run back in and retrieve it. We were very pleased with the whole experience. Thank you to the owners of the condo for making your vacation home a welcoming place. You made a wise choice when you selected Winter Park Lodging Company to be your property management team. We would definitely recommend both!
MANAGER COMMENTS: Wow! Many thanks for writing all this up Raelene. We appreciate you taking the time and are all so pleased you enjoyed your stay. We would love to host you again whenever you end up back this way.
By Milton, Posted: 09/05/2018We found our stay in Trailhead Lodge inviting and very relaxing. The staff was very friendly and professional, from making our reservation until after check-out. They followed up a couple of times during our stay, to be sure everything was satisfactory. We found condo exceptionally clean, updated and furnished with everything you could possibly need. The location for us was perfect,close to restaurants, entertainment and shopping. We highly recommend Winter Park Lodging Company to anyone who would be visiting in the area.
MANAGER COMMENTS: Wonderful! We are so pleased it was a great spot for you. We hope you will contact us when your travels bring you back this way.
By Robert, Posted: 08/07/2018We had a great time at the Trailhead Lodge. The rooms were cleaned. The kitchen had everything to prepare a meal. The price was a bit too high but overall it was a good experience staying there.
MANAGER COMMENTS: We thank you for coming to stay with us at 2018 Jazz Fest. Those Trailhead properties are the most popular for their direct location/access to the festival venue. We are so pleased you were able to book early with us for 2019 to ensure the best pricing Robert See you then!
By Maria, Posted: 04/16/2018Trips to Winter Park with Winter Park Lodging Company, and specifically at Trailhead Lodges, never disappoints. We started our Spring Break at another mountain town and it paled in comparison. We felt so welcome, right at home and incredibly taken care of. Thank you for ending our ski season on such a positive note!!
MANAGER COMMENTS: Awesome! That's so wonderful to hear. It's what we all love about Winter Park...it's an easy place to be and enjoy. We hope you come back with us again.
By Tisha, Posted: 03/05/2018The unit was beautiful and what a great location! It was central to everything and the bus lift to the mountain was just a few steps away. Cozy fireplace, which we used often. Wonderful kitchen and we cooked in everyday. We will most definitely rent again.
MANAGER COMMENTS: Thanks Tish! We are all so pleased you enjoyed Trailhead 811 with us. We look forward to hosting you again.
By Sarah, Posted: 02/13/2018I have been booking with Winter Park Lodging Company for two years now. They are the most professional and courteous rental company I have ever dealt with.
MANAGER COMMENTS: Well thanks! That's so great to hear. We love ya back! Can't wait to host you again Sarah.
By Sonia, Posted: 11/11/2017Quick weekend getaway. So much room and cozy. Had a wonderful leaf-peeping weekend in the mountains. Hope to come back for skiing. THank you, Sonia
MANAGER COMMENTS: Thanks Sonia! So glad you were able to visit at such a pretty time of year. Let us know when you're back this way again.
Q: Is there covered parking?A: Trailhead Lodges complex has all open air parking spaces.
Q: Is the pool open all year round?A: The outdoor heated pool and hot tub are open all year round.
Q: How far do you have to walk to access the clubhouse, pool and hot tub?A: The clubhouse is about 20 steps from your front door!