$0
for 0 nights

Home in Winter Park, CO

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

  • Free parking
  • Gym
  • Dryer
  • Washer
  • EV Charger
  • Laundromat nearby
  • Mountain view
  • 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

4.3 · 9 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

Restaurants

Randi's Grill & Pub

Nestled in Winter Park, Randi's Irish Grill & Pub blends authentic Irish specialties like shepherd's pie and fish & chips with American classics, all made fresh with local ingredients. Unwind in this lively sports bar with fireplaces, 7 HD TVs, and perfectly poured pints in a fun, family-friendly vibe.[1][2][3][4][5]

The Ditch on 40

Nestled in Winter Park, The Ditch on 40 is a family-run roadside bar and grill dishing up authentic New Mexican cuisine with Hatch chile flair, killer burgers, sandwiches, and the town's best margaritas in a lively dive-bar vibe.

Deno's Mountain Bistro

Nestled in a historic stagecoach stop turned Winter Park chophouse since 1976, Deno's Mountain Bistro offers aged grass-fed steaks, Mediterranean flair, and award-winning wines in a cozy mountain lodge vibe. Savor classics like burrata caprese or bison short ribs with impeccable service after a day on the slopes.

Hernando's Pizza Pub

Nestled in Winter Park since 1967, Hernando's Pizza Pub serves homemade pizzas, pasta, and Italian classics in a cozy ski-town hideaway adorned with $40,000 in signed dollar bills. Warm fireplaces and lively vibes make it a beloved tradition for locals and visitors alike.

Devil's Thumb Ranch Resort & Spa

Nestled in the Colorado mountains, Devil's Thumb Ranch Resort & Spa serves farm-to-fork modern ranch fare like Ranch-raised Wagyu beef and fresh herbs from on-site gardens. Savor it by a grand stone fireplace or with stunning Continental Divide views in a rustic 1930s homestead.

Wake N' Bacon

Wake 'n Bacon is Chicago's Instagram-famous brunch haven in Lakeview, blending Asian, Latin, and American flavors into photogenic dishes like Ube Flapjacks and Bacon Flights. Floor-to-ceiling florals, a playful photo wall, and vibrant vibes make every meal a celebration.

Sharky's Eatery

Sharky's Eatery serves hearty breakfast and lunch favorites like enormous pancakes, hefty omelets, and juicy burgers with homemade strawberry-raspberry jam, all day long. Nestled in downtown Fraser's quaint alpine rustic vibe, it's the perfect cozy spot to dig in with mimosas or fresh coffee.

Attractions

Winter Park Resort

Soar up Winter Park Resort's scenic gondola for free on winter evenings to the mountaintop après at Sunspot, where live music, tasty specials, and epic Rocky Mountain views create unforgettable vibes. Families, friends, and adventure seekers love this chill yet lively way to cap the day.[4]

Fraser Tubing Hill

Since 1971, the Historic Fraser Tubing Hill has delivered thrilling snow tubing rides on a family-owned slope with a magic carpet lift—no skills needed. Families, groups, and young thrill-seekers love its low-key fun, cozy fireplace, and nighttime excitement.

Trestle Bike Park

Trestle Bike Park delivers over 40 miles of lift-served thrills in Colorado's mountains, blending jumps, flowy blues, and gnarly tech lines for every rider from nervous newbies to pro shredders. Families and gravity junkies alike will love its endless progression and stunning peak views.[1][2][3][5]

Cooper Creek Square

Discover the charm of Cooper Creek Square, Winter Park's lantern-lit outdoor plaza blending eclectic shops with handmade artisan treasures and global cuisines around a cozy fire pit. Families, fashion lovers, and mountain adventurers will adore this vibrant hub of local vibes and unique finds.[1][2][3][5]

Fraser Valley Sports Complex

Discover year-round thrills at Fraser Valley Sports Complex, from the NHL-sized Icebox rink and sand volleyball to a historic Western playground amid stunning mountain views. Sports enthusiasts, families, and pickleball fans will love this scenic outdoor haven.[1][2][3][5]

Rendezvous Event Center

Rendezvous Event Center is a vibrant downtown Winter Park hub featuring a skate park, playground, and year-round activities, from free summer concerts and live music to winter sledding with provided sleds—perfect for families seeking outdoor fun and community entertainment.

Fraser Valley Distilling

Discover Fraser Valley Distilling, a family-owned mountain gem crafting small-batch spirits like gin, vodka, and whiskey influenced by high-altitude precision and local grains, paired with scratch-kitchen bites and craft cocktails. Skiers, hikers, and spirit lovers will savor its laid-back après vibe in cozy Fraser, Colorado.[1][2][3]

Coca Cola Tubing Hill At Winter Park

Fly down thrilling banked curves on the four-lane Coca-Cola Tube Hill at Winter Park, with a covered conveyor effortlessly whisking you back to the top for endless fun. Families, thrill-seekers, and non-skiers of all ages (36"+) will love this no-skills-required snowy adventure.[1][3][4][5]

Hideaway Park

Nestled in downtown Winter Park's Rocky Mountains, Hideaway Park transforms seasonally into a sledding hill with free sleds and fire pits in winter, or a vibrant amphitheater for summer concerts, skate park, and climbing wall. Families, outdoor enthusiasts, and kids of all ages adore its year-round fun and central vibe.[1][2][5]

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
Sep 2, 2026$200Available
Sep 3, 2026$200Available
Sep 4, 2026$199Available
Sep 5, 2026$199Not Available
Sep 6, 2026$199Not Available
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Sep 10, 2026$199Available
Sep 11, 2026$199Available
Sep 12, 2026$199Available
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Sep 14, 2026$199Available
Sep 15, 2026$199Available
Sep 16, 2026$199Available
Sep 17, 2026$199Available
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Sep 19, 2026$200Available
Sep 20, 2026$200Available
Sep 21, 2026$200Available
Sep 22, 2026$200Available
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Sep 24, 2026$200Available
Sep 25, 2026$200Available
Sep 26, 2026$199Available
Sep 27, 2026$199Available
Sep 28, 2026$200Available
Sep 29, 2026$199Available
Sep 30, 2026$200Available
Oct 1, 2026$200Available
Oct 2, 2026$199Available
Oct 3, 2026$199Available
Oct 4, 2026$199Available
Oct 5, 2026$199Available
Oct 6, 2026$199Available
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Oct 9, 2026$199Available
Oct 10, 2026$200Available
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Oct 14, 2026$199Available
Oct 15, 2026$199Available
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Oct 20, 2026$200Available
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Oct 24, 2026$199Available
Oct 25, 2026$199Available
Oct 26, 2026$200Available
Oct 27, 2026$200Available
Oct 28, 2026$200Available
Oct 29, 2026$199Available
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Oct 31, 2026$200Available
Nov 1, 2026$200Available
Nov 2, 2026$200Available
Nov 3, 2026$200Available
Nov 4, 2026$199Available
Nov 5, 2026$200Available
Nov 6, 2026$231Available
Nov 7, 2026$237Available
Nov 8, 2026$199Available
Nov 9, 2026$199Available
Nov 10, 2026$200Available
Nov 11, 2026$199Available
Nov 12, 2026$199Available
Nov 13, 2026$228Available
Nov 14, 2026$227Available
Nov 15, 2026$199Available
Nov 16, 2026$200Available
Nov 17, 2026$199Available
Nov 18, 2026$200Available
Nov 19, 2026$201Available
Nov 20, 2026$245Available
Nov 21, 2026$272Not Available
Nov 22, 2026$270Not Available
Nov 23, 2026$282Not Available
Nov 24, 2026$297Not Available
Nov 25, 2026$337Not Available
Nov 26, 2026$343Not Available
Nov 27, 2026$346Not Available
Nov 28, 2026$310Available
Nov 29, 2026$255Available
Nov 30, 2026$248Available
Dec 1, 2026$249Available