3 bedrooms
•
3 beds
•
2.5 bathrooms
•
8 guests
•
New
•
2200 sq. ft.
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
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
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Winter Park, CO 80482, US
Winter Park, CO, USNestled 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]
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.
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.
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.
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 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 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.
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]
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 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]
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]
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 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.
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]
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]
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]
Cancel within 24 hours for a full refund.
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 |
|---|---|---|
| Jun 18, 2026 | $278 | Available |
| Jun 19, 2026 | $276 | Available |
| Jun 20, 2026 | $278 | Available |
| Jun 21, 2026 | $278 | Available |
| Jun 22, 2026 | $278 | Available |
| Jun 23, 2026 | $276 | Available |
| Jun 24, 2026 | $278 | Available |
| Jun 25, 2026 | $278 | Available |
| Jun 26, 2026 | $304 | Available |
| Jun 27, 2026 | $304 | Available |
| Jun 28, 2026 | $304 | Available |
| Jun 29, 2026 | $278 | Available |
| Jun 30, 2026 | $276 | Available |
| Jul 1, 2026 | $278 | Available |
| Jul 2, 2026 | $276 | Available |
| Jul 3, 2026 | $305 | Available |
| Jul 4, 2026 | $305 | Available |
| Jul 5, 2026 | $305 | Available |
| Jul 6, 2026 | $305 | Available |
| Jul 7, 2026 | $276 | Available |
| Jul 8, 2026 | $278 | Available |
| Jul 9, 2026 | $276 | Available |
| Jul 10, 2026 | $276 | Available |
| Jul 11, 2026 | $278 | Available |
| Jul 12, 2026 | $276 | Available |
| Jul 13, 2026 | $276 | Available |
| Jul 14, 2026 | $276 | Available |
| Jul 15, 2026 | $276 | Available |
| Jul 16, 2026 | $276 | Available |
| Jul 17, 2026 | $304 | Available |
| Jul 18, 2026 | $327 | Available |
| Jul 19, 2026 | $331 | Available |
| Jul 20, 2026 | $276 | Available |
| Jul 21, 2026 | $278 | Available |
| Jul 22, 2026 | $278 | Available |
| Jul 23, 2026 | $276 | Available |
| Jul 24, 2026 | $276 | Not Available |
| Jul 25, 2026 | $276 | Not Available |
| Jul 26, 2026 | $278 | Not Available |
| Jul 27, 2026 | $278 | Not Available |
| Jul 28, 2026 | $278 | Not Available |
| Jul 29, 2026 | $278 | Not Available |
| Jul 30, 2026 | $276 | Not Available |
| Jul 31, 2026 | $276 | Not Available |
| Aug 1, 2026 | $276 | Available |
| Aug 2, 2026 | $278 | Available |
| Aug 3, 2026 | $278 | Available |
| Aug 4, 2026 | $278 | Available |
| Aug 5, 2026 | $276 | Available |
| Aug 6, 2026 | $278 | Available |
| Aug 7, 2026 | $278 | Available |
| Aug 8, 2026 | $276 | Available |
| Aug 9, 2026 | $276 | Available |
| Aug 10, 2026 | $276 | Available |
| Aug 11, 2026 | $278 | Available |
| Aug 12, 2026 | $278 | Available |
| Aug 13, 2026 | $276 | Available |
| Aug 14, 2026 | $276 | Available |
| Aug 15, 2026 | $276 | Available |
| Aug 16, 2026 | $276 | Available |
| Aug 17, 2026 | $278 | Available |
| Aug 18, 2026 | $278 | Available |
| Aug 19, 2026 | $276 | Available |
| Aug 20, 2026 | $276 | Available |
| Aug 21, 2026 | $278 | Available |
| Aug 22, 2026 | $276 | Available |
| Aug 23, 2026 | $276 | Available |
| Aug 24, 2026 | $278 | Available |
| Aug 25, 2026 | $276 | Available |
| Aug 26, 2026 | $276 | Available |
| Aug 27, 2026 | $276 | Available |
| Aug 28, 2026 | $276 | Available |
| Aug 29, 2026 | $276 | Available |
| Aug 30, 2026 | $276 | Available |
| Aug 31, 2026 | $278 | Available |
| Sep 1, 2026 | $276 | Available |
| Sep 2, 2026 | $276 | Available |
| Sep 3, 2026 | $278 | Available |
| Sep 4, 2026 | $353 | Available |
| Sep 5, 2026 | $353 | Available |
| Sep 6, 2026 | $352 | Available |
| Sep 7, 2026 | $304 | Available |
| Sep 8, 2026 | $278 | Available |
| Sep 9, 2026 | $276 | Available |
| Sep 10, 2026 | $278 | Available |
| Sep 11, 2026 | $276 | Available |
| Sep 12, 2026 | $276 | Available |
| Sep 13, 2026 | $276 | Available |
| Sep 14, 2026 | $278 | Available |
| Sep 15, 2026 | $276 | Available |
| Sep 16, 2026 | $278 | Available |