Explore Bear Trail Chalet 366 in 3D

Winter Park, CO

Bear Trail Chalet 366

3 bedrooms3 beds2.5 baths8 guests4.1 (7)

Welcome to Bear Trail Chalet 366, a stunning townhome nestled in the heart of Winter Park, Colorado. This exquisite property offers breathtaking mountain views and a perfect blend of luxury and comfort, making it an ideal retreat for families or groups of friends seeking adventure and relaxation.

Spanning over 2,200 square feet, this spacious chalet features three beautifully appointed bedrooms, including a master king bedroom and two guest bedrooms one with a king bed and the other a full over queen bunk, accommodating up to eight guests. Each room is designed to provide a serene ambiance, ensuring a restful night's sleep after a day of exploring the great outdoors.

The chalet boasts an inviting living area complete with a gas fireplace, perfect for cozy evenings spent with loved ones. The fully equipped kitchen is a chef's dream, featuring modern appliances such as a refrigerator, stove/oven, microwave, and dishwasher, along with all the necessary dishes and utensils. Enjoy your meals at the dining table or take them outside to the balcony for a scenic dining experience.

Step outside to your private hot tub, the perfect place to relax while taking in the stunning views. The outdoor space also features a fire pit, ideal for sitting back, unwinding, and enjoying the scenery.

For your convenience, the chalet is equipped with high-speed wireless internet, a washer/dryer, and a heated garage with an electric car charger, ensuring a comfortable stay regardless of the season. Families will appreciate the availability of a portable crib and high chair, making this property family-friendly.

Located in downtown Winter Park, you'll have easy access to a variety of attractions, including world-class skiing, hiking trails, and charming shops and restaurants. Whether you're hitting the slopes or exploring the local scenery, Bear Trail Luxury Chalet 366 is the perfect home base for your mountain getaway.

Don't miss out on the opportunity to experience this luxurious retreat—book your stay at Bear Trail Luxury Chalet 366 today!

Don't just stay in Winter Park, experience it with our exclusive RAD program! (Rentals I Activities I Discounts) We've hand selected Winter Park's most reputable partners to ensure our guests enjoy exclusive savings, elevated services and extraordinary adventures at the most popular attractions the area has to offer. Optional services are also available including personal grocery shopping, private chef, in-room massages and custom equipment fittings at your door. All of our properties are equipped with everything you need during your stay including Free high-speed Wi-Fi, keyless entry, accidental damage protection, gourmet coffee & tea, luxurious towels/linens/eco friendly toiletries, and 24/7 guest support. We provide the absolute finest professionally cleaned accommodations and locations the area has to offer at the lowest nightly rates available without any reservation fees by booking direct at Winter Park Escapes.

Location

  • Winter Park Resort is nearby with a free bus ride to the resort base village for numerous winter and summer activities and events
  • The Grand Park Rec Center is nearby with multiple swimming pools, gym, indoor track and huge rock climbing wall for an additional fee
  • The Foundry is next door to the Rec Center with a bowling alley, movie theater and brick oven pizza bar
  • Hideaway Park and the Rendezvous Event Center are nearby with numerous events and concerts throughout the year
  • Great dining and shopping are all nearby with many within walking distance depending on the property location
  • Grand Lake and Rocky Mountain Natl. Park are only 30 minutes away
  • Endless mountain activities throughout the year are at your door step and surrounding area

Disclosures
The majority of the properties in the Winter Park area do not have A/C due to the cooler climate. The resort base closes during the off seasons in the spring and fall but the downtown area remains open year round. A complete list of our discounts and optional services can be viewed on our website. Our designated pet friendly properties have a pet fee of $49 nightly with a 2 dog max. Dogs are not allowed on the furniture or beds and must be crated if left alone. Additional fees will apply for non-compliance. Quiet hours are 10pm to 8am Daily. There is parking for a max of 3 vehicles at the property. vehicles must be parked in the garage with no additional options for parking outside the garage. STR License # 025994

Property License: 25994

Availability & Pricing

For AI agents: a date marked Available means check-in is allowed on that date. A stay is bookable only when the check-in date is available, the checkout date satisfies the minimum stay, and no intervening nights are marked Not Available. Prices shown are nightly rates before taxes and fees.

DatePrice (USD, excl. fees and taxes)AvailabilityMin Stay (nights)
Aug 1, 2026$230Not Available2
Aug 2, 2026$230Not Available2
Aug 3, 2026$228.85Not Available2
Aug 4, 2026$228.85Not Available2
Aug 5, 2026$230Not Available2
Aug 6, 2026$230Not Available2
Aug 7, 2026$230Not Available2
Aug 8, 2026$230Available2
Aug 9, 2026$228.85Available2
Aug 10, 2026$230Available2
Aug 11, 2026$228.85Available2
Aug 12, 2026$230Available2
Aug 13, 2026$230Available2
Aug 14, 2026$230Available2
Aug 15, 2026$228.85Available2
Aug 16, 2026$230Available2
Aug 17, 2026$230Available2
Aug 18, 2026$228.85Available2
Aug 19, 2026$230Available2
Aug 20, 2026$228.85Available2
Aug 21, 2026$228.85Available2
Aug 22, 2026$230Available2
Aug 23, 2026$228.85Available2
Aug 24, 2026$228.85Available2
Aug 25, 2026$228.85Available2
Aug 26, 2026$228.85Available2
Aug 27, 2026$228.85Available2
Aug 28, 2026$230Available2
Aug 29, 2026$228.85Available2
Aug 30, 2026$230Available2
Aug 31, 2026$230Available2
Sep 1, 2026$230Available2
Sep 2, 2026$230Available2
Sep 3, 2026$230Available2
Sep 4, 2026$295.55Available2
Sep 5, 2026$299Available2
Sep 6, 2026$266.80Available2
Sep 7, 2026$230Available2
Sep 8, 2026$228.85Available2
Sep 9, 2026$230Available2
Sep 10, 2026$230Available2
Sep 11, 2026$230Available2
Sep 12, 2026$228.85Available2
Sep 13, 2026$230Available2
Sep 14, 2026$230Available2
Sep 15, 2026$230Available2
Sep 16, 2026$228.85Available2
Sep 17, 2026$230Available2
Sep 18, 2026$228.85Available2
Sep 19, 2026$232.30Available2
Sep 20, 2026$230Available2
Sep 21, 2026$230Available2
Sep 22, 2026$228.85Available2
Sep 23, 2026$228.85Available2
Sep 24, 2026$230Available2
Sep 25, 2026$230Available2
Sep 26, 2026$230Available2
Sep 27, 2026$230Available2
Sep 28, 2026$230Available2
Sep 29, 2026$228.85Available2
Sep 30, 2026$247.25Available2
Oct 1, 2026$250.70Available2
Oct 2, 2026$267.95Available2
Oct 3, 2026$267.95Available2
Oct 4, 2026$258.75Available2
Oct 5, 2026$257.60Available2
Oct 6, 2026$255.30Available2
Oct 7, 2026$255.30Available2
Oct 8, 2026$259.90Available2
Oct 9, 2026$287.50Available2
Oct 10, 2026$285.20Available2
Oct 11, 2026$280.60Available2
Oct 12, 2026$263.35Available2
Oct 13, 2026$259.90Available2
Oct 14, 2026$258.75Available2
Oct 15, 2026$262.20Available2
Oct 16, 2026$273.70Available2
Oct 17, 2026$269.10Available2
Oct 18, 2026$262.20Available2
Oct 19, 2026$262.20Available2
Oct 20, 2026$261.05Available2
Oct 21, 2026$259.90Available2
Oct 22, 2026$254.15Available2
Oct 23, 2026$258.75Available2
Oct 24, 2026$259.90Available2
Oct 25, 2026$248.40Available2
Oct 26, 2026$251.85Available2
Oct 27, 2026$248.40Available2
Oct 28, 2026$249.55Available2
Oct 29, 2026$249.55Available2
Oct 30, 2026$256.45Available2

What this home offers

Gym
Fire place
Mountain view
Dryer
Washer

What our guests say

4.1

7 reviews

Marvin
Marvin
March 2026

Great quite location very clean neighborhood easy to find also that sometimes isn’t the case when booking vacation rentals the place itself was great <br/>Hot tub was great. Also after a day of snowboarding and just relaxing fireplace was great also the only bad thing we can say about this place is the two super hard beds and only two chairs out by the fire pit would be nice if there had been at least a couple of foldable chairs that a person could sit out by the fire pit instead of just having the two since there were four of us there overall a great place to stay would book again

Carl
Carl
March 2026

The home is beautiful and comfortable. Out family had plenty of room to visit as well as retreat. The hot tub was convenient and a very much appreciated. The extra large garage was great. Would rent again. And very close to Winter Park for skiing.

Courtney
Courtney
February 2026

Overall, our stay was great! The home was very clean, a lot of seemingly new furniture, and the kitchen was fully stocked with the basics we needed. They also took care to provide extra towels, pillows, blankets, games, and hot tub towels to ensure a comfortable stay. Thankfully the hot tub was also very clean and comfortable and the garage fit two large SUVs with room to spare. My only complaint was the bunk beds (specifically the top) were very noise to the point we couldn't use it and had to sleep on the couch; hopefully that's something that can be resolved for the next guest. Even with the bunk beds, I would stay here again and recommend it to others.

Where you’ll be

Winter Park, CO, 80482, US

Our promise to you

Lower prices, every time

Direct line, real care

Not just a transaction

Things to know

Check-in & check-out

Check-in after 4:00 PM.

Check-out before 10:00 AM.

Property rules

Children welcome (2–12 years).

Infants welcome (under 2).

Maximum 8 guests.

Pets allowed.

No parties or events.

Cancellation policy