Trailhead Lodges 821 - Stay Winter Park

Location

Description

Trailhead 821 is an excellent destination for families and is pet friendly, offering a sledding hill suitable for all ages, as well as fire pits for warming up at the Rendezvous Event Center. In the summer, visitors can enjoy the skate park and outdoor gymnasium. The property is conveniently accessible via the free town shuttle, making it an ideal retreat for couples, small families or solo travelers in search of comfortable lodging.
A convenient stroll to the main street offers year-round dining and shopping opportunities. During the summer months, the Rendezvous Event Center transforms into a vibrant hub featuring live music, craft fairs, fitness events, situated adjacent to this charming one-bedroom unit.
The primary bedroom features a King-sized bed along with a flat screen TV. In addition, the living room is furnished with a new Queen sofa sleeper, providing extra sleeping accommodations. The living room also includes a flat screen TV, a gas fireplace and access to a private deck.
The well-equipped kitchen is designed for both casual cooking and gourmet meal preparation. This spacious and light-filled area is conveniently located next to the dining area and opens up to the main living room. Additionally, the hallway leads to a full bathroom and a gear room suitable for ski storage and similar items. A private deck offers a view of downtown, while the unit does not include air conditioning and features a private washer and dryer.
Situated on the second floor of the building, guests may utilize the shared elevator for convenient access. PARKING: Only two designated spots are available.
The Trailhead Lodge clubhouse offers a variety of on-site amenities, including an outdoor grilling area, a game room, a fitness room, a hot tub and an outdoor pool, available throughout the year.
Smoking is prohibited. The regulations set forth by the Homeowner Association explicitly forbids guests from smoking on the premises. These regulations are rigorously enforced. Any guests found smoking on the property will incur a fine of 200 for each day of violation.
WPSTR license: STR#20390

Specials

Spring stay savings

Spring in Winter Park comes with perks—save on your stay when you book direct with Stay Winter Park. 🏔️

Save 10% off 1–2 nights: Use promo code SPRING10 at check out

Save 15% off 3+nights: Use promo code SPRING15 at check out

*Offers are valid on new bookings when you book by April 28, 2026. Bookings must meet the specified minimum stay requirements to qualify for the discount(s) from February 12, 2026–April 30, 2026. Cannot be combined with other offers.

Call us at 1-800-215-6535, book online, or email us at [email protected] to book your Winter Park Getaway!

*Offer expires 04/27/2026 and you must book your vacation between 02/12/2026 and 04/30/2026.

Save on weekday Winter Park stays

Make the most of midweek in Winter Park. Enjoy extra savings on Sunday–Thursday stays, and secure the best pricing to enjoy skiing, restaurants and shopping without the crowds.

Save 20% off 1+ nights: Use promo code MW20 at check out

*Offer is valid on new online bookings when you book by May 19, 2026 for 1+ night stays from February 12–May 21, 2026. Cannot be combined with other offers. Other exclusions and restrictions may apply to select properties.

Call us at 1-800-215-6535, book online, or email us at [email protected] to book your Winter Park Getaway!

*Offer expires 05/19/2026 and you must book your vacation between 02/12/2026 and 05/21/2026.

Availability Calendar

Available

Unavailable

Check-In

Check-Out

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Swipe for Availability

Rooms

Living room

Sleeps: 2

1 Sofa Sleeper

kitchen

Dining area

Primary bedroom

Sleeps: 2

1 King Bed

Primary bathroom

Amenities 60

BBQ Area
Bed Linens
Car not needed - public transportation
Carbon Monoxide Detector
Check In - keyless entry
Coffee Maker
Dishes & Silverware
Dishwasher
Dryer
Elevator - common to building
Extra Pillows & Blankets
Fire Extinguisher
First Aid Kit
Fishing
Free Parking - outdoor
Game Room
Games
Golf
Grill
Gym/Fitness Room
Hair Dryer
Heating
Hiking
Home Step Free Access
Hot tub - clubhouse outdoor
Hot Water
Kitchen
Laptop Friendly
Level - second floor unit
Living Room
Microwave
NO air conditioning
No laundry
Oven
Parking Pass required
Path to Entrance Lit at Night
Patio or balcony - private
Pool - clubhouse outdoor
Pool Table
Private Entrance
Private Living Room
Refrigerator
Satellite or Cable
Shampoo
Shopping
Smoke Detector
Snowmobiling
Snowtubing
Stove
Television
Toaster
Towels
Washer
Wireless Internet
Work station - computer set up, desk

Fireplace

Fireplace - gas

View

View - Continental Divide

Downtown Winter Park
Hot tub - common area outdoor
Pet Friendly

Reviews 4.9 (70)

It was perfect for our small family and small pup. Very clean with all the amenities we needed
Michele - Posted: 4/3/2026

Thank you for the five-star review! Glad the space was perfect for your family and pup and that it was very clean with everything you needed. We appreciate you choosing Stay Winter Park and would love to host you again.
Stay Winter Park staff

This is a perfect little condo, very clean and comfy, easy to get to Winter Park and close to restaurants.
Sarah - Posted: 3/24/2026

Thank you for your 5-star review, Sarah! Glad the condo was clean, comfy, and convenient for getting to Winter Park and nearby restaurants. We’d love to host you again.
Stay Winter Park staff

We had a great stay at this cozy condo. The location is great - walkable to the bus stop for the ski area, walkable to good restaurants. It's a busy condo area but felt very comfortable, quiet, nice neighborhood. Loved the gas fireplace and all the nice windows. Lots of light.
Carol - Posted: 3/1/2026

Thank you for the five-star review! Glad you had a great stay in the cozy condo and that the location — an easy walk to the bus stop and restaurants — worked well. Happy the gas fireplace, bright windows, and quiet neighborhood made your visit comfortable. We’d love to host you again.
Stay Winter Park staff

The host was welcoming, the unit very clean, and we loved that it was pet friendly. Great access to shuttle and downtown Winterpark.
Verified traveler - Posted: 2/26/2026

Thank you for the 5-star review! We’re happy you enjoyed your stay and would love to host you again.
Stay Winter Park staff

Great location, well stocked kitchen, and comfortable and cozy place. We so enjoyed our time.
Sharon - Posted: 1/25/2026

Thank you for the five-star review! Glad the location, well-stocked kitchen, and cozy, comfortable space met your needs. We’re happy you enjoyed your time and would love to host you again.
Stay Winter Park staff

We had a wonderful quick stay at this property. The unit was super clean, welcoming and well stocked. The location was great for access to restaurants and also the ski resort.
Katie - Posted: 1/20/2026

Thank you for your 5-star review! Glad you had a wonderful quick stay and found the unit super clean, welcoming, and well stocked. Happy it was convenient for restaurants and the ski resort — we’d love to host you again.
Stay Winter Park staff

The location of this condo was fantastic! So close to Winter Park resort, downtown shops and restaurants, and right across the street from a park. Inside was very spacious for our group of friends and dog and the pullout sofa was surprisingly comfortable. Only 1 parking pass comes with this condo but we were able to leave our extra car in the free garage across the street no problem. Would stay here again!
Emily - Posted: 1/3/2026

Didn’t use pool but looked nice
Frank - Posted: 12/27/2025

Thank you for the 5-star review! We’re happy you enjoyed your stay and would love to host you again.
Stay Winter Park staff

Beautiful and spacious condo downtown, equip with all your needs. I would definitely stay here again. Super close to the resort.
Johana - Posted: 12/25/2025

We had a great stay! Loved everything about it, was super cozy, comfortable and had everything we needed and more! Also great location for winter park for skiing! I would definitely come back and recommend this place to anyone needing a getaway, thank you again!
Ashley - Posted: 12/9/2025

Thank you for the 5-star review! We’re happy you enjoyed your stay and would love to host you again.
Stay Winter Park staff

The host was super responsive! The place was gorgeous and very spacious. It was perfect for us and very walkable!
Hailey - Posted: 12/7/2025

Amazing location and very helpful hosts! I stayed here with my friends for an early season ski trip and it was perfect. Would love to stay again.
Calla - Posted: 12/1/2025

We had a great stay here! The location is perfect and very centralized for downtown Winter Park. The condo was clean and well-maintained. We had great communication from the hosts so check-in and check-out was seamless. Would love to stay here again.
Emily - Posted: 11/17/2025

Thank you for the 5-star review! We’re happy you enjoyed your stay and would love to host you again.
Stay Winter Park staff

We had a great stay in Winter park! Lodging was as described and comfortable. We loved the location and would return.
Teri - Posted: 10/7/2025

Thank you for your 5-star review! We’re glad you enjoyed your stay and hope to welcome you back soon!
Stay Winter Park staff

Wonderful clean property!
Madison - Posted: 10/2/2025

Thanks for the five-star review! Glad you found the property wonderful and clean, we’d be happy to host you again anytime.
Stay Winter Park staff

Great location and a very nice place to stay.
Gloria - Posted: 10/1/2025

Great condo

Great little condo with everything you need.
Shannon R from Redstone Historical District, CO - Posted: 9/15/2025

Thank you for your 5 star review
Stay Winter Park staff

Posted: 9/25/2025

We have stayed here a couple of times now. Great location. Worth the price & dog friendly!
Dean - Posted: 9/2/2025

Thanks for the great review! We'd love to host you again soon!
Stay Winter Park staff

Would definitely stay here again!

Great area, comfortable space, accessible to restaurants, bars, and trails. Check in was easy. Would definitely stay here again.
Megan S from Littleton, CO - Posted: 8/13/2025

Thank you for your review and we're very happy to know that you had a great stay and we look forward to hosting you again
Stay Winter Park staff

Posted: 8/18/2025

Great property

Easy check in, great property!
Robin W from Omaha, NE - Posted: 8/13/2025

Thank you for your 5 star review
Stay Winter Park staff

Posted: 8/18/2025

Great area, comfortable space, accessible to restaurants, bars, and trails. Check in was easy. Would definitely stay here again.
Megan - Posted: 8/10/2025

Thank you for your review!
Stay Winter Park staff

Easy check in, great property!
Robin - Posted: 8/8/2025

Thank you for your review, we'd love to host you again!
Stay Winter Park staff

Close to the venues

We appreciated the gas fireplace in the living room (even in August when it's cool at night). The condos are right next to the main city park and we heard concerts and events most mornings, but the unit faces away from the park so it wasn't noisy inside. The host was very communicative and informative about check in.
Jerod S from Los Ranchos de Albuquerque, NM - Posted: 8/4/2025

Thank you for your review and feedback. We are very happy to hear that you enjoyed so many things about our rental, had a great stay and that our staff was able to assist you with all of your questions
Stay Winter Park staff

Posted: 8/5/2025

Great Airbnb. We appreciated the gas fireplace in the living room (even in August when it's cool at night). The condos are right next to the main city park and we heard concerts and events most mornings, but the Airbnb faces away from the park so it wasn't noisy inside. The host was very communicative and informative about check in.
Jerod - Posted: 8/3/2025

Thanks for the great review! We'd love to host you again soon!
Stay Winter Park staff

Great location

Comfortable condo with a great location, easy to walk to town.
John M from Aurora, CO - Posted: 7/28/2025

Thank you for your 5 star review
Stay Winter Park staff

Posted: 7/29/2025

Nice stay in Winter Park

Comfortable condo with a great location, easy to walk to town.
John - Posted: 7/28/2025

Thank you for your review!
Stay Winter Park staff

Perfect place

We enjoyed our time very much. There is a lovely balcony to sit outside. The location was perfect. The bed was very comfortable, and the kitchen was well stocked. We’d highly recommend, and would stay there again!
Penny F from Fort Collins, CO - Posted: 7/22/2025

Thank you for your review and we love to hear that you had such a wonderful stay with us and look forward to hosting you again. We appreciate your recommendation to others
Stay Winter Park staff

Posted: 7/25/2025

We enjoyed our time very much. There is a lovely balcony to sit outside. The location was perfect. The bed was very comfortable, and the kitchen was well stocked. We’d highly recommend, and would stay there again!
Penny - Posted: 7/17/2025

Thank you so much—we’re thrilled you enjoyed your stay and would love to host you again!
Stay Winter Park staff

Good location.
Kenneth - Posted: 7/10/2025

Thanks for the 5 stars review!
Stay Winter Park staff

Great location, very spacious.
William - Posted: 6/22/2025

Thank you for your review!
Stay Winter Park staff

Great location!

This condo has a great location, the downtown area is within walking distance. The area is very pet friendly.
Mark - Posted: 6/21/2025

Thanks for your review! We're glad you enjoyed the location and that it worked well for you and your pet.
Stay Winter Park staff

Great Stay

Place was clean and as described. Bed was very comfortable. Would definitely stay here again. Check in and checkout was easy.
Nate - Posted: 5/5/2025

Thanks so much for the kind words! We're happy you enjoyed the comfy bed and smooth check-in. We'd love to host you again at Stay Winter Park!
Stay Winter Park staff

[email protected]

Great vacation
Bonnie H from Valdosta GA - Posted: 4/21/2025

Thank you for your 5 star review
Stay Winter Park staff

Posted: 4/21/2025

Good property.as described

Everything as described. We had a great, but quick one night stay.
Jennifer A from Littleton CO - Posted: 4/10/2025

Thank you for your 5 star review
Stay Winter Park staff

Posted: 4/10/2025

Winter Park

Great vacation
Bonnie - Posted: 4/7/2025

Thank you for your 5 star review
Stay Winter Park staff

Outstanding

The place was very clean and very nice. Great location and family friendly. Great space. Seemed well insulated for noise. Can't say enough good things. I would recommend it
Mike T from Valley Center KS - Posted: 4/3/2025

Thank you for your review and we're so happy to know you had a great stay with us
Stay Winter Park staff

Posted: 4/3/2025

Good property.as described

Everything as described. We had a great, but quick one night stay.
Jennifer - Posted: 3/28/2025

Thank you for your 5 star review
Stay Winter Park staff

Outstanding

The place was very clean and very nice. Great location and family friendly. Great space. Seemed well insulated for noise. Can't say enough good things.Two comments that are not complaints, just things to note if you are going to rent.1 The bedroom bed is very high off the ground. My wife had to use the window sill to get a push into bed.2 The pull out bed mattress is not the greatest, but not the worst. Would be ok for kids but adults might not like it. I slept on it one night and my back was a bit sore the next day. I would recommend it.
Mike - Posted: 3/24/2025

Thank you for your review and feedback. We are very happy that overall you had a great stay and we will share your feedback on the bedding with our housekeeping manager to see if we can upgrade the pull out bed mattress.
Stay Winter Park staff

Would absolutely book again

I was impressed with how large the apartment was and how clean the kitchen (dishes and such) and bed linens were. I’m REALLY picky with those things. It felt very cozy and clean. We went with our 2yo and loved the park across the street! It was a great place to take him for his introduction to a snowboard
Audra M from Plano TX - Posted: 2/19/2025

Thank you for your review and we love to hear that you had such a great stay with us and enjoyed the area.
Stay Winter Park staff

Posted: 2/19/2025

I was impressed with how large the apartment was and how clean the kitchen (dishes and such) and bed linens were. I’m REALLY picky with those things. It felt very cozy and clean.
We went with our 2yo and loved the park across the street! It was a great place to take him for his introduction to a snowboard.
Would absolutely book again.
Audra - Posted: 2/17/2025

Thank you for your review and feedback. We love to hear that you had such a great stay and your 2yo got to experience the winter activities. We look forward to hosting you again.
Stay Winter Park staff

Excellent property

Excellent property.
Louise N from Fulham Gardens SA Australia - Posted: 2/4/2025

Thank you for you review
Stay Winter Park staff

Posted: 2/4/2025

Great stay!

Love the fully stocked kitchen. Nice nice. Very comfortable.
Sue Ann B from Boulder CO - Posted: 1/20/2025

Thank you for your 5 star review
Stay Winter Park staff

Posted: 1/20/2025

Great stay!

Love the fully stocked kitchen. Nice nice. Very comfortable.
Sue Ann - Posted: 1/9/2025

Thank you for your 5 star review and we're very happy to hear that you had a great stay with us.
Stay Winter Park staff

Excellent

The location is excellent and I have had many good rental experiences in this complex.
Chris M from Durham NC - Posted: 1/7/2025

Thank you for your 5 star review
Stay Winter Park staff

Posted: 1/7/2025

Good place

The place and location was great
Andrew H from Aurora CO - Posted: 11/12/2024

Thank you for your review
Stay Winter Park staff

Posted: 11/12/2024

Nice

Nice downtown location, easy walking.
Shawn O from Laramie WY - Posted: 11/4/2024

Thank you for your review and we're very happy to hear that you enjoyed your stay and the downtown area.
Stay Winter Park staff

Posted: 11/4/2024

Great place! We will be back!
Travis - Posted: 11/3/2024

Nice downtown location, easy walking.
Shawn - Posted: 11/3/2024

Than you for your review and we're very happy to hear that you enjoyed your stay with us and the downtown area.
Stay Winter Park staff

Weekend getaway for hiking and fishing. Perfect all around

Location, Communication, Style Pet friendly Na
Huxley - Posted: 10/22/2024

Great location

Great location; within short walking distance to many fantastic restaurants and shopping areas.
Diana I from Norman OK - Posted: 9/23/2024

Thank you for your 5 star review!
Stay Winter Park staff

Posted: 9/23/2024

Great location and very cozy

Always great staying with you guys! Thanks! Would stay again!
James H from Golden CO - Posted: 9/10/2024

Thank you for your review and we love to hear that you always have a wonderful stay with us and look forward to hosting you again.
Stay Winter Park staff

Posted: 9/10/2024

Great location!

Near all the good restaurants and shops and if you’re going to an event at Rendezvous center it’s perfect!
Savannah H from Boulder CO - Posted: 8/19/2024

Thank you for your review and love to hear you enjoyed our condo and all of the great spots in downtown WP.
Stay Winter Park staff

Posted: 8/19/2024

Great location! Near all the good restaurants and shops and if you’re going to an event at Rendezvous center it’s perfect!
Savannah - Posted: 8/11/2024

Thank you for your review and we love to hear you had a great stay and enjoyed being close to all of the downtown attractions.
Stay Winter Park staff

Great place

Great Airbnb with a giant comfy bed in the bedroom. And impeccably clean.
Katheryn S from Denver CO - Posted: 8/1/2024

Thank you for your 5 star review!
Stay Winter Park staff

Posted: 8/1/2024

Great Airbnb with a giant comfy bed in the bedroom. And impeccably clean.
But warning to those sleeping on the pullout. The bed unfolds, but there is not enough space for it to fully unfold so the end of it lays on top of the other couch. This causes a slight bow which made the bed pretty uncomfortable. Very odd layout for the pullout, the other living room couch is either too big or the pullout is.
Katheryn - Posted: 7/19/2024

Thank you for your review and feedback. We are glad that you enjoyed your stay and will share your feedback on the pullout bed with our management team so that we can adjust the layout and make this more comfortable for future guests.
Stay Winter Park staff

Perfect 1 bedroom in the heart of it all!

Perfect location, great clubhouse and pool. I'd highly recommend.
Kirsch - Posted: 5/9/2024

Downtown Deal

Great location in downtown Winter Park. Spacious, clean condo with a deck and partial mountain view. Very well stocked with paper products, towels and kitchen supplies. Check in and check out times (4PM in and 10AM out) but the management company was gracious and called to let us know the condo was ready and we could check in early at 3:30.
Tina - Posted: 4/13/2024

Thank you for your review and feedback. We are so happy to hear that you enjoyed so many things for your getaway with us and we were glad to help accommodate an earlier check in for you.
Stay Winter Park staff

Very nice place

As described. Very nice place for a weekend getaway to ski.
Mike G from Omaha NE - Posted: 4/9/2024

Thank you for your review
Stay Winter Park staff

Posted: 4/9/2024

As described. Very nice place for a weekend getaway to ski.
Mike - Posted: 4/7/2024

Thank you for your review
Stay Winter Park staff

We had a great weekend!

We really enjoyed our stay. The condo was very nice and clean. The bed was comfortable and especially liked the heated floors and fireplace. Easy walk or bike ride to anywhere in the area.
Jim F from Greeley CO - Posted: 10/23/2023

Thank you for your review and we love to hear you had such a great with stay us and in the area!
Stay Winter Park staff

Posted: 10/23/2023

Great spot!

Great spot in a great location! Clean and roomy. Would definitely stay there again!
Aaron W from Blacksburg VA - Posted: 10/23/2023

Thank you for your review and very happy to hear you enjoyed our condo and look forward to hosting you again
Stay Winter Park staff

Posted: 10/23/2023

Great spot in a great location!
Clean and roomy. Would definitely stay there again!
Aaron - Posted: 10/18/2023

Thank you for your review and we are happy you enjoyed your stay and look forward to hosting you again!
Stay Winter Park staff

We really enjoyed our stay. The condo was very nice and clean. The bed was comfortable and especially liked the heated floors and fireplace. Easy walk or bike ride to anywhere in the area.
Jim - Posted: 10/15/2023

Thank you for your review. We love to hear you enjoyed our condo and your stay with us.
Stay Winter Park staff

Great place!

Had a little confusion about the travel crib but they were quick to respond and took care of it right away. Definitely recommend staying here!
Andrew S from Ft Collins CO - Posted: 10/4/2023

Thank you for your review and glad our staff was able to quickly assist you. We appreciate your recommendation to others.
Stay Winter Park staff

Posted: 10/5/2023

Great place! Had a little confusion about the travel crib but they were quick to respond and took care of it right away. Definitely recommend staying here!
Andrew - Posted: 10/2/2023

Thank you for your review and we're sorry to hear about the travel crib but glad we were able to promptly get this taken care of for you. We appreciate your recommendation to others.
Stay Winter Park staff

Very clean well maintained condo. Kitchen was well stocked with all utensils, China, etc. Waser and dryer was a bonus!!
David - Posted: 9/26/2023

We enjoyed our stay at this condo.

It's in the perfect location, with easy parking access. Check-in instructions were clear. The condo was clean, spacious and perfect for our stay.
Maggie G from Topeka KS - Posted: 9/21/2023

Thank you for your review and we're very happy to hear that you had such a great stay with us!
Stay Winter Park staff

Posted: 9/25/2023

We enjoyed our stay at this condo. It's in the perfect location, with easy parking access. Check-in instructions were clear. The only part of the process that was not as smooth was the need to create a user name on the 'Stay' portal to access all information including check-in information. It made everything a 3-4 step process vs. being able to find all the information on the Airbnb app. The condo was clean, spacious and perfect for our stay.
Maggie - Posted: 9/15/2023

Thank you for your review and feedback. We are happy to hear that you enjoyed the condo and your stay with us. We are disappointed to hear that the steps needed for the portal weren't 100% smooth for you and will work with our management team to see if we can improve this.
Stay Winter Park staff

Easy booking!

The door code is sent through another source and site (Stay), so that was a bit tricky to navigate. But overall the place was very affordable and clean!
Daniel H from Highlands Ranch CO - Posted: 4/28/2023

Thank you for your review and we are glad that you enjoyed the unit and your stay with us. We will see if we can improve the door code process as well.
Stay Winter Park staff

Posted: 4/28/2023

Easy booking! The door code is sent through another source and site (Stay), so that was a bit tricky to navigate. But overall the place was very affordable and clean!
Daniel - Posted: 4/23/2023

Thank you for your review and feedback. We are glad that you enjoyed the unit and your stay with us. We will share your feedback on the door code with management to see if we can improve this process.
Stay Winter Park staff

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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?"

Are there any units available that face Rendezvous park? What units would be in that area? Appreciate your time, Dzrae

Dzrae B - Posted: 03/23/2024

Answer:

Our units at this property are on the back side of the complex and unfortunately do not face the Event Center. We do offer several units.

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