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Downtown WP Chalet 366 I Private Hot Tub I Great Views I Arcade I Discounted Attractions
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Reviews
9.8 out of 10
Exceptional
3 bedrooms2+ bathroomsSleeps 8204.4 sq m
Popular amenities
Explore the area

Winter Park, CO
- Place, Hideaway Park16 min walk
- Place, Winter Park Visitor Center16 min walk
- Place, Bella Vita18 min walk
Rooms & beds
3 bedrooms (sleeps 8)
Guest Bunkroom
1 Single Bunk Bed
Guest King Bedroom
1 King Bed
Master King Bedroom
1 King Bed
2 bathrooms, 2 half bathrooms
Entrance Level Powder Bath
Toilet
Hallway Bathroom
Bathtub or shower · Bathtub · Toilet
Main Floor Powder Bath
Toilet
Master King Ensuite Bathroom
Toilet · Shower only
Spaces
Deck or patio
Kitchen
Balcony
Separate dining area
Dining area
About this property
Downtown WP Chalet 366 I Private Hot Tub I Great Views I Arcade I Discounted Attractions
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
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
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10.0 out of 10, Exceptional, (3 reviews)
House Rules
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
Pets allowed
Smoking
Smoking is not permitted
Important information
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
About the area
Winter Park
Located in Winter Park, this holiday home is in the city centre and in the mountains. Hideaway Park and The Fraser River Trail reflect the area's natural beauty and area attractions include Amaze'n Maze Winter Park and Alpine Slide. Make sure you get close to the area's animals with activities such as game walks and birdwatching.

Winter Park, CO
What's nearby
- Hideaway Park - 16 min walk - 1.4 km
- Winter Park Visitor Center - 16 min walk - 1.4 km
- Bella Vita - 18 min walk - 1.6 km
- Blue Sky Massage - 20 min walk - 1.7 km
- Grand Park Community Recreation Center - 3 min drive - 2.6 km
Getting around
Restaurants
- Wake N’ Bacon - 4 min drive
- The Noble Buck - 4 min drive
- McDonald's - 3 min drive
- Wendy's - 7 min drive
- Snoasis - 12 min drive
Frequently asked questions
Reviews
9.8
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window9.6/10
Cleanliness
10/10
Check-in
9.2/10
Communication
10/10
Location
10/10
Listing accuracy
Reviews
Verified
2 Dec 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 4 nights in Nov 2025
From a partner site
10/10 Excellent
Scott M.
24 Jan 2026
Great location and villa was better than expected.
Scott M.
Verified
10/10 Excellent
Cecil W.
13 Jan 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy
Cecil W.
Stayed 6 nights in Jan 2026
Verified
10/10 Excellent
Scott B.
30 July 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Scott B.
Stayed 2 nights in Jul 2025
Verified
8/10 Good
julie r.
27 Dec 2025
Liked: Cleanliness, check-in, location, listing accuracy
julie r.
Stayed 7 nights in Dec 2025
Verified
10/10 Excellent
Deborah W.
8 Feb 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy


Deborah W.
Stayed 7 nights in Jan 2026
Verified
10/10 Excellent
Marc O.
3 Sept 2025
Marc O.
Stayed 4 nights in Aug 2025
About the host
Hosted by Winter Park Escapes
Winter Park Escapes is the premier local full service rental management company specializing in luxury vacation rentals in the Winter Park area for over 20 years, voted best in the county for consecutive years along with the award for the top 10 in the Country. All of our hand picked rentals provide premium locations and views, and include many upgraded features and amenities that are not available in other vacation rentals. Our homes are equipped with everything you need for your stay including our exclusive RAD program (Rentals, Activities, Discounts) that provides discounts for local activities, restaurants, equipment rentals and transportation at some of the most popular attractions the area has to offer to provide a 5 star experience that can't be matched.
Languages:
English
Premier Host
They consistently provide great experiences for their guests
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