Bear Den is a cozy townhouse tucked into the Bear Crossing neighborhood of Winter Park. It boasts beautiful alpine views, comfortable spaces to gather, multiple fireplaces and a location that's just a short drive to Winter Park Resort. With over 2,100 square feet, three bedrooms and 3.5 bathrooms, there's plenty of room for your group to spread out while still having a cozy place to come together after a day on the slopes or trails.

Head inside to the main level living room and settle into the comfortable seating while taking in the incredible mountain views through the large windows. The stone-hearth gas fireplace is the perfect place to warm up after a day outside, while the open layout keeps the living room connected to the dining area and kitchen. Whether you're catching up around the fire, watching a movie or simply enjoying the views, this is a great space to relax and spend time together.

The kitchen is ready for the chef in your group with granite countertops, stainless steel appliances and a large island with seating. There's also a coffee station, juicer and crock-pot, making it easy to prepare everything from a quick breakfast before hitting the slopes to a big dinner with the whole group. Gather around the dining table for dinner or head out onto one of the private balconies to enjoy the crisp mountain air and surrounding views.

Ready to rest easy? The upper level hosts the King Primary Suite, complete with a two-way fireplace and private balcony overlooking the mountains. The ensuite bathroom features a jetted garden tub, glass shower and double vanity, creating a relaxing retreat at the end of the day. Across the hall is another private King Suite with its own gas fireplace, ensuite bathroom, soaking tub and walk-in closet.

The lower level offers a Twin bedroom with two Twin beds and its own full ensuite bathroom, making it a great setup for kids or friends traveling together. There's also a downstairs living room with a Queen sofa bed, giving your group an additional place to relax or providing extra sleeping space when needed. With bedrooms spread across multiple levels, everyone can find their own space while still having plenty of room to come together.

When you're ready to get outside, Bear Den puts you close to everything Winter Park has to offer. Winter Park Resort is approximately 3 miles away, with the free resort shuttle stop about a 5–10 minute walk from the home. Downtown Winter Park and Hideaway Park are both approximately a five-minute drive, making it easy to head into town for dinner, shopping, live music and other mountain-town fun.
Additional amenities include private balconies, mountain views, multiple fireplaces, jetted tubs, a fully equipped kitchen, single-car attached garage, additional driveway parking, Wi-Fi and premium hotel-style linens. Bear Den is a great home base for a family or group looking for a comfortable mountain retreat with plenty of space and easy access to Winter Park Resort.

Sleeping Arrangements: King Primary Suite on upper level, King Suite in the second bedroom on upper level, Two Twin beds and Queen sofa bed in the downstairs living room. Sleeps up to eight guests.

Location: Approximately 1 mile from the main street of Downtown Winter Park. Approximately three miles to Winter Park Resort (Walk to free bus shuttle, but not a suitable walk for kids).

Local Deals: Save on local adventurous activities, gear rentals, transportation, and more when booking with us. Discount codes will be sent after booking.

Please Note:
- No smoking allowed.
- Reservation holder must be 25 years or older.
- Check-in: 4:00pm, Check-out: 10:00am
- Guest will be required to sign a Winter Park Lodging Company rental agreement within 48 hours of booking.
- Quiet Hours: 10:00pm-8:00am. Please respect your neighbors, many of which live nearby year-round.
- Like many mountain communities, you may occasionally hear nearby construction, train activity, snow removal or normal neighborhood activity.

Parking: Single-car attached garage and spot in driveway.​​​​​​​

RENTAL LICENSE NO: 007164

The Winter Park Lodging Company Difference

24/7 Local Help: Book with confidence knowing that the rates, images and details published on this property are 100% accurate. We are conveniently headquartered in Winter Park, this provides us with a local advantage to take care of any issue or need that may arise during your stay, 24/7. If any questions, needs or concerns arise just call us and we will be there at your door to make it right.
Keyless Lock: This home is equipped with a Smart Lock, allowing easy, secure access to your property at check-in and throughout your stay. There's no need to check in at a separate location!
What's Included: Every home is stocked with all your household essentials, high quality sheets and towels, and a starter kit of high-end bathroom products, and an ample supply of laundry detergent, trash bags, dish soap, tissues, etc.
We're Following the Rules: This vacation rental is professionally managed and follows all local & state tax rules. Your reservation total includes all applicable taxes, cleaning fee, and Accidental Property Damage Protection.
Clean & Safe: Keeping our vacation homes sparkling clean is a top priority at Winter Park Lodging Company. All properties are cleaned, sanitized & disinfected before guests check-in with products proven to eliminate viruses & bacteria. All linens are laundered at an offsite facility that meets commercial standards. Additionally, the entirety of our housekeeping processes meet and exceed CDC cleaning guidelines. If you have any questions/concerns, please reach out to our Vacation Planners for more details.