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Home in Winter Park, CO

Bear Trail Chalet 366

3 bedrooms

3 beds

2.5 bathrooms

8 guests

2200 sq. ft.

Operated by a Wander partner

Trusted operators, vetted by Wander

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
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

Property License: 25994

Amenities

Common Amenities

  • Mountain view
  • Dryer
  • Washer
  • EV Charger
  • Laundromat nearby
  • Massage table
  • Private Chef
  • Crib
  • Coffee maker

Bathroom 1

  • Hair dryer

Bathroom 2

  • Bath linens

Bedroom 1

  • Bed linens

Living room

  • Fire place
  • Heating
  • TV

Garage

  • Garage

Common area

  • Wifi

Laundry room

  • Ironing board

Dining room

  • Dining table
  • High chair

Kitchen

  • Dishes
  • Dishwasher
  • Kitchen
  • Microwave
  • Oven
  • Fridge
  • Spices
  • Stove
  • Toaster
  • Ice maker

Pool

  • Hot tub

5.0 · 7 reviews

G

Guy

August 2026

Property was easy to find and within walking distance from the event center in town. Large garage space for 2 vehicles and gear. Nice kitchen, furnishings were comfortable. Slept great on a comfortable bed, and what a beautiful view to look out upon when we opened the shades in the morning! Would definitely stay here again.
C

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.
B

Brandon

January 2026

Beautiful home right near everything. Main strip with restaurants and ski rental five minutes away and Winter Park Resort only ten minutes away. We skied the whole time so it was nice to come home to the hot tub and a big clean house to relax in.

Where you’ll be

Winter Park, CO 80482, US

Winter Park, CO, US
39.914499-105.796427
Timezone: America/Denver

Things to know

Cancellation policy

Free cancellation up to 14 days before check-in. No refund after that.

Property rules

Pets allowed with fee

No smoking - fees will apply

Events not allowed

Safety & security

Check-in after 4:00 pm

Check-out before 10:00 am

8 guests maximum

Availability & Pricing

DatePrice (USD, excl. fees and taxes)Availability
Oct 3, 2026$200Available
Oct 4, 2026$199Available
Oct 5, 2026$199Available
Oct 6, 2026$199Available
Oct 7, 2026$199Available
Oct 8, 2026$200Available
Oct 9, 2026$199Available
Oct 10, 2026$200Available
Oct 11, 2026$200Available
Oct 12, 2026$199Available
Oct 13, 2026$200Available
Oct 14, 2026$199Available
Oct 15, 2026$199Available
Oct 16, 2026$199Available
Oct 17, 2026$200Available
Oct 18, 2026$199Available
Oct 19, 2026$200Available
Oct 20, 2026$199Available
Oct 21, 2026$200Available
Oct 22, 2026$199Available
Oct 23, 2026$199Available
Oct 24, 2026$200Available
Oct 25, 2026$199Available
Oct 26, 2026$200Available
Oct 27, 2026$199Available
Oct 28, 2026$199Available
Oct 29, 2026$199Available
Oct 30, 2026$199Available
Oct 31, 2026$200Available
Nov 1, 2026$200Available
Nov 2, 2026$199Available
Nov 3, 2026$200Available
Nov 4, 2026$199Available
Nov 5, 2026$199Available
Nov 6, 2026$200Available
Nov 7, 2026$199Available
Nov 8, 2026$199Available
Nov 9, 2026$199Available
Nov 10, 2026$199Available
Nov 11, 2026$199Available
Nov 12, 2026$199Available
Nov 13, 2026$200Available
Nov 14, 2026$200Available
Nov 15, 2026$199Available
Nov 16, 2026$199Available
Nov 17, 2026$200Available
Nov 18, 2026$200Available
Nov 19, 2026$200Available
Nov 20, 2026$207Available
Nov 21, 2026$232Not Available
Nov 22, 2026$229Not Available
Nov 23, 2026$241Not Available
Nov 24, 2026$255Not Available
Nov 25, 2026$280Not Available
Nov 26, 2026$290Not Available
Nov 27, 2026$295Not Available
Nov 28, 2026$258Available
Nov 29, 2026$219Available
Nov 30, 2026$210Available
Dec 1, 2026$233Available
Dec 2, 2026$239Available
Dec 3, 2026$243Available
Dec 4, 2026$268Available
Dec 5, 2026$273Available
Dec 6, 2026$261Available
Dec 7, 2026$262Available
Dec 8, 2026$274Available
Dec 9, 2026$279Available
Dec 10, 2026$295Available
Dec 11, 2026$319Available
Dec 12, 2026$328Available
Dec 13, 2026$308Available
Dec 14, 2026$305Available
Dec 15, 2026$314Available
Dec 16, 2026$330Available
Dec 17, 2026$355Available
Dec 18, 2026$621Available
Dec 19, 2026$622Available
Dec 20, 2026$765Available
Dec 21, 2026$828Available
Dec 22, 2026$824Available
Dec 23, 2026$885Available
Dec 24, 2026$899Available
Dec 25, 2026$914Available
Dec 26, 2026$909Available
Dec 27, 2026$1057Available
Dec 28, 2026$1072Available
Dec 29, 2026$1059Available
Dec 30, 2026$1016Available
Dec 31, 2026$1017Available
Jan 1, 2027$1213Available