Winter Park, CO

Bear Trail Chalet 366

3 bedrooms 3 beds 3 baths 8 guests New

About the property

Welcome to Bear Trail Luxury 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 Luxury 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.

Date Price (USD, excl. fees and taxes) AvailabilityMin Stay (nights)
May 19, 2026$238.80Available2
May 20, 2026$238.80Available2
May 21, 2026$238.80Available2
May 22, 2026$264Available2
May 23, 2026$264Available2
May 24, 2026$262.80Available2
May 25, 2026$262.80Available2
May 26, 2026$238.80Available2
May 27, 2026$238.80Available2
May 28, 2026$240Available2
May 29, 2026$240Available2
May 30, 2026$238.80Available2
May 31, 2026$238.80Available2
Jun 1, 2026$238.80Available2
Jun 2, 2026$240Available2
Jun 3, 2026$238.80Available2
Jun 4, 2026$238.80Available2
Jun 5, 2026$238.80Available2
Jun 6, 2026$240Available2
Jun 7, 2026$238.80Available2
Jun 8, 2026$240Available2
Jun 9, 2026$240Available2
Jun 10, 2026$238.80Available2
Jun 11, 2026$240Available2
Jun 12, 2026$240Available2
Jun 13, 2026$240Available2
Jun 14, 2026$238.80Available2
Jun 15, 2026$240Available2
Jun 16, 2026$238.80Available2
Jun 17, 2026$238.80Available2
Jun 18, 2026$240Available2
Jun 19, 2026$240Available2
Jun 20, 2026$240Available2
Jun 21, 2026$238.80Available2
Jun 22, 2026$240Available2
Jun 23, 2026$238.80Available2
Jun 24, 2026$238.80Available2
Jun 25, 2026$240Available2
Jun 26, 2026$262.80Available2
Jun 27, 2026$264Available2
Jun 28, 2026$262.80Available2
Jun 29, 2026$238.80Available2
Jun 30, 2026$240Available2
Jul 1, 2026$240Available2
Jul 2, 2026$262.80Available2
Jul 3, 2026$295.20Available2
Jul 4, 2026$301.20Available2
Jul 5, 2026$264Available2
Jul 6, 2026$262.80Available2
Jul 7, 2026$238.80Available2
Jul 8, 2026$238.80Available2
Jul 9, 2026$240Available2
Jul 10, 2026$238.80Available2
Jul 11, 2026$240Available2
Jul 12, 2026$240Available2
Jul 13, 2026$240Available2
Jul 14, 2026$238.80Available2
Jul 15, 2026$238.80Available2
Jul 16, 2026$240Available2
Jul 17, 2026$476.40Available3
Jul 18, 2026$583.20Available3
Jul 19, 2026$506.40Available3
Jul 20, 2026$302.40Available2
Jul 21, 2026$282Available2
Jul 22, 2026$292.80Available2
Jul 23, 2026$306Available2
Jul 24, 2026$300Not Available2
Jul 25, 2026$301.20Not Available2
Jul 26, 2026$279.60Not Available2
Jul 27, 2026$289.20Not Available2
Jul 28, 2026$289.20Not Available2
Jul 29, 2026$283.20Not Available2
Jul 30, 2026$278.40Not Available2
Jul 31, 2026$283.20Not Available2
Aug 1, 2026$277.20Available2
Aug 2, 2026$268.80Available2
Aug 3, 2026$255.60Available2
Aug 4, 2026$252Available2
Aug 5, 2026$254.40Available2
Aug 6, 2026$261.60Available2
Aug 7, 2026$261.60Available2
Aug 8, 2026$255.60Available2
Aug 9, 2026$244.80Available2
Aug 10, 2026$238.80Available2
Aug 11, 2026$238.80Available2
Aug 12, 2026$238.80Available2
Aug 13, 2026$238.80Available2
Aug 14, 2026$241.20Available2
Aug 15, 2026$238.80Available2
Aug 16, 2026$238.80Available2
Aug 17, 2026$238.80Available2

Amenities

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

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Where you'll be

Winter Park, CO, 80482, US

Things to know

Cancellation policy

Contact us for cancellation policy details prior to booking.

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.