Winter Park, CO

Bear Trail Chalet 366

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

About the property

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

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

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)
Jul 3, 2026$222Not Available2
Jul 4, 2026$220.89Not Available2
Jul 5, 2026$222Not Available2
Jul 6, 2026$222Not Available2
Jul 7, 2026$220.89Not Available2
Jul 8, 2026$220.89Available2
Jul 9, 2026$222Available2
Jul 10, 2026$220.89Available2
Jul 11, 2026$220.89Available2
Jul 12, 2026$222Available2
Jul 13, 2026$220.89Available2
Jul 14, 2026$220.89Available2
Jul 15, 2026$220.89Available2
Jul 16, 2026$222Available2
Jul 17, 2026$222Available2
Jul 18, 2026$220.89Available2
Jul 19, 2026$220.89Available2
Jul 20, 2026$222Available2
Jul 21, 2026$220.89Available2
Jul 22, 2026$222Available2
Jul 23, 2026$220.89Available2
Jul 24, 2026$220.89Not Available2
Jul 25, 2026$220.89Not Available2
Jul 26, 2026$220.89Not Available2
Jul 27, 2026$222Not Available2
Jul 28, 2026$220.89Not Available2
Jul 29, 2026$220.89Not Available2
Jul 30, 2026$220.89Not Available2
Jul 31, 2026$222Not Available2
Aug 1, 2026$222Available2
Aug 2, 2026$220.89Available2
Aug 3, 2026$222Available2
Aug 4, 2026$222Available2
Aug 5, 2026$222Available2
Aug 6, 2026$222Available2
Aug 7, 2026$220.89Available2
Aug 8, 2026$220.89Available2
Aug 9, 2026$220.89Available2
Aug 10, 2026$222Available2
Aug 11, 2026$220.89Available2
Aug 12, 2026$222Available2
Aug 13, 2026$222Available2
Aug 14, 2026$220.89Available2
Aug 15, 2026$222Available2
Aug 16, 2026$220.89Available2
Aug 17, 2026$222Available2
Aug 18, 2026$222Available2
Aug 19, 2026$220.89Available2
Aug 20, 2026$220.89Available2
Aug 21, 2026$222Available2
Aug 22, 2026$222Available2
Aug 23, 2026$220.89Available2
Aug 24, 2026$220.89Available2
Aug 25, 2026$222Available2
Aug 26, 2026$222Available2
Aug 27, 2026$222Available2
Aug 28, 2026$222Available2
Aug 29, 2026$222Available2
Aug 30, 2026$220.89Available2
Aug 31, 2026$220.89Available2
Sep 1, 2026$220.89Available2
Sep 2, 2026$258.63Available2
Sep 3, 2026$265.29Available2
Sep 4, 2026$337.44Available2
Sep 5, 2026$338.55Available2
Sep 6, 2026$336.33Available2
Sep 7, 2026$293.04Available2
Sep 8, 2026$258.63Available2
Sep 9, 2026$261.96Available2
Sep 10, 2026$256.41Available2
Sep 11, 2026$261.96Available2
Sep 12, 2026$263.07Available2
Sep 13, 2026$249.75Available2
Sep 14, 2026$239.76Available2
Sep 15, 2026$241.98Available2
Sep 16, 2026$243.09Available2
Sep 17, 2026$251.97Available2
Sep 18, 2026$258.63Available2
Sep 19, 2026$263.07Available2
Sep 20, 2026$246.42Available2
Sep 21, 2026$243.09Available2
Sep 22, 2026$251.97Available2
Sep 23, 2026$238.65Available2
Sep 24, 2026$256.41Available2
Sep 25, 2026$267.51Available2
Sep 26, 2026$273.06Available2
Sep 27, 2026$253.08Available2
Sep 28, 2026$241.98Available2
Sep 29, 2026$240.87Available2
Sep 30, 2026$239.76Available2
Oct 1, 2026$244.20Available2

Amenities

Gym
Fire place
Mountain view
Dryer
Washer
EV Charger
Laundromat nearby
Massage table

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

Cancellation policy

Property rules

Children welcome (2–12 years).
Infants welcome (under 2).
Pets allowed.
No parties or events.

Safety & security

Check-in after 4:00 PM.
Check-out before 10:00 AM.
Maximum 8 guests.