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7 reviews
Operated by a Wander partner
Trusted operators, vetted by Wander
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
Disclosures
This property allows up to 2 dogs only for an additional fee of $49 nightly. Dogs are not allowed on the furniture or beds and must be crated if left alone. Additional fees will apply for non compliance. 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. 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
Guy
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August 2026
Courtney
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February 2026
Brandon
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January 2026
Winter Park, CO 80482, US
Winter Park, CO, USFree cancellation up to 14 days before check-in. No refund after that.
Pets allowed with fee
No smoking - fees will apply
Events not allowed
Check-in after 4:00 pm
Check-out before 10:00 am
8 guests maximum
| Date | Price (USD, excl. fees and taxes) | Availability |
|---|---|---|
| Oct 3, 2026 | $200 | Available |
| Oct 4, 2026 | $199 | Available |
| Oct 5, 2026 | $199 | Available |
| Oct 6, 2026 | $199 | Available |
| Oct 7, 2026 | $199 | Available |
| Oct 8, 2026 | $200 | Available |
| Oct 9, 2026 | $199 | Available |
| Oct 10, 2026 | $200 | Available |
| Oct 11, 2026 | $200 | Available |
| Oct 12, 2026 | $199 | Available |
| Oct 13, 2026 | $200 | Available |
| Oct 14, 2026 | $199 | Available |
| Oct 15, 2026 | $199 | Available |
| Oct 16, 2026 | $199 | Available |
| Oct 17, 2026 | $200 | Available |
| Oct 18, 2026 | $199 | Available |
| Oct 19, 2026 | $200 | Available |
| Oct 20, 2026 | $199 | Available |
| Oct 21, 2026 | $200 | Available |
| Oct 22, 2026 | $199 | Available |
| Oct 23, 2026 | $199 | Available |
| Oct 24, 2026 | $200 | Available |
| Oct 25, 2026 | $199 | Available |
| Oct 26, 2026 | $200 | Available |
| Oct 27, 2026 | $199 | Available |
| Oct 28, 2026 | $199 | Available |
| Oct 29, 2026 | $199 | Available |
| Oct 30, 2026 | $199 | Available |
| Oct 31, 2026 | $200 | Available |
| Nov 1, 2026 | $200 | Available |
| Nov 2, 2026 | $199 | Available |
| Nov 3, 2026 | $200 | Available |
| Nov 4, 2026 | $199 | Available |
| Nov 5, 2026 | $199 | Available |
| Nov 6, 2026 | $200 | Available |
| Nov 7, 2026 | $199 | Available |
| Nov 8, 2026 | $199 | Available |
| Nov 9, 2026 | $199 | Available |
| Nov 10, 2026 | $199 | Available |
| Nov 11, 2026 | $199 | Available |
| Nov 12, 2026 | $199 | Available |
| Nov 13, 2026 | $200 | Available |
| Nov 14, 2026 | $200 | Available |
| Nov 15, 2026 | $199 | Available |
| Nov 16, 2026 | $199 | Available |
| Nov 17, 2026 | $200 | Available |
| Nov 18, 2026 | $200 | Available |
| Nov 19, 2026 | $200 | Available |
| Nov 20, 2026 | $207 | Available |
| Nov 21, 2026 | $232 | Not Available |
| Nov 22, 2026 | $229 | Not Available |
| Nov 23, 2026 | $241 | Not Available |
| Nov 24, 2026 | $255 | Not Available |
| Nov 25, 2026 | $280 | Not Available |
| Nov 26, 2026 | $290 | Not Available |
| Nov 27, 2026 | $295 | Not Available |
| Nov 28, 2026 | $258 | Available |
| Nov 29, 2026 | $219 | Available |
| Nov 30, 2026 | $210 | Available |
| Dec 1, 2026 | $233 | Available |
| Dec 2, 2026 | $239 | Available |
| Dec 3, 2026 | $243 | Available |
| Dec 4, 2026 | $268 | Available |
| Dec 5, 2026 | $273 | Available |
| Dec 6, 2026 | $261 | Available |
| Dec 7, 2026 | $262 | Available |
| Dec 8, 2026 | $274 | Available |
| Dec 9, 2026 | $279 | Available |
| Dec 10, 2026 | $295 | Available |
| Dec 11, 2026 | $319 | Available |
| Dec 12, 2026 | $328 | Available |
| Dec 13, 2026 | $308 | Available |
| Dec 14, 2026 | $305 | Available |
| Dec 15, 2026 | $314 | Available |
| Dec 16, 2026 | $330 | Available |
| Dec 17, 2026 | $355 | Available |
| Dec 18, 2026 | $621 | Available |
| Dec 19, 2026 | $622 | Available |
| Dec 20, 2026 | $765 | Available |
| Dec 21, 2026 | $828 | Available |
| Dec 22, 2026 | $824 | Available |
| Dec 23, 2026 | $885 | Available |
| Dec 24, 2026 | $899 | Available |
| Dec 25, 2026 | $914 | Available |
| Dec 26, 2026 | $909 | Available |
| Dec 27, 2026 | $1057 | Available |
| Dec 28, 2026 | $1072 | Available |
| Dec 29, 2026 | $1059 | Available |
| Dec 30, 2026 | $1016 | Available |
| Dec 31, 2026 | $1017 | Available |
| Jan 1, 2027 | $1213 | Available |