Villa with Private Hot Tub, Mountain Views & Free Activities

Discover a private villa at 865 Bear Trail that combines the comfort of a single-family home with exclusive resort-style perks. Enjoy a private hot tub, sweeping mountain views, and easy access to Winter Park Resort, recreation centers, and downtown attractions. With curated complimentary adventures and family-focused enhancements, this spacious retreat is designed for families, adventure seekers, and groups seeking both relaxation and excitement. Experience amenities and local activities that shift with the seasons—all in a location that places you at the heart of Winter Park’s best offerings.

10 10 guests
3 3 bedrooms
3.5 3.5 bathrooms
Winter Park Winter Park, Colorado
The image showcases the villa's striking architecture with colorful balconies surrounded by lush foliage, bathed in the warm glow of sunset. The inviting exterior hints at cozy winter nights by the fireplace and vibrant summer evenings spent relaxing on the porch, with plenty of space for outdoor gatherings and family fun.
Savor spectacular sunsets and mountain air from vibrant balconies—your perfect retreat for cozy nights and unforgettable adventures in the heart of Winter Park.

Private hot tub with mountain views, exclusive complimentary adventures, family-friendly amenities, close to resort and rec center, spacious upscale design.

Mountain Gathering Haven

Features

  • • Large windows with scenic mountain views
  • • Gas fireplace
  • • Contemporary mountain decor
  • • Private patio
  • • Plush seating
  • • Private hot tub
  • • Living room opens to dining area and patio

Step into the heart of your Rocky Mountain escape, where laughter echoes around the fireplace and large windows reveal scenic mountain views. The open-concept living room, dining area, and private patio seamlessly merge to create a dynamic hub for connection—perfect for family game nights, après-ski stories, or toasting to adventure with friends. Contemporary mountain decor invites relaxation, while the crackling gas fireplace and plush seating make every gathering feel comfortable and stylish. Step outside to the patio for a morning coffee or evening soak in the private hot tub, taking in views that change with the seasons.

A cozy living room with a prominent gas fireplace, large leather sofas arranged around a coffee table, a patterned rug, and expansive windows revealing scenic mountain views. The space is bathed in warm light, highlighting the contemporary mountain decor and inviting atmosphere for group gatherings.
Gather around the fireplace and take in sweeping mountain views from the plush comfort of the living room.
A stylish dining area centered around a wooden table set for a meal, with large artwork on the wall and a sliding wooden door leading out to the patio. The space feels welcoming and ideal for family dinners or celebrations, seamlessly connecting to the outdoors.
Share memorable meals in a dining space that flows effortlessly to the outdoor patio.
An inviting wooden deck featuring a private hot tub, surrounded by yellow autumn foliage. The deck offers serene views of nature, ideal for a peaceful morning coffee or a relaxing soak after a day of adventure.
Relax in the private hot tub while soaking in breathtaking mountain scenery from the patio.

Chef’s Domain & Family Feast

Features

  • • Modern appliances
  • • Locally roasted gourmet coffee
  • • Spacious dining table
  • • Open kitchen layout
  • • Kitchen connected to living and dining area

Fuel your adventures in a chef’s kitchen designed for both gourmet flair and easy family meals. The fully equipped kitchen, featuring modern appliances and thoughtful extras like locally roasted gourmet coffee, is the heart of culinary creativity. Gather at the spacious dining table for hearty breakfasts before hitting the slopes, quick lunches between adventures, or lingering family dinners that stretch into game night. The kitchen’s layout and amenities make meal prep a breeze, and its proximity to the living and dining spaces keeps everyone connected—whether you’re whipping up snacks or indulging in takeout from downtown.

This interior image features an inviting kitchen scene with a central kitchen island, warm wooden cabinets, stainless steel appliances, and a visible dining area in the background. The space is clearly designed for both meal preparation and social gatherings, offering modern amenities and an open layout that keeps the kitchen connected to the dining area.
Gather around the open kitchen island and enjoy family meals or festive culinary creations in a space designed for togetherness.
This interior image presents a stylish and friendly kitchen and dining area, featuring a kitchen island, an elegant chandelier, a spacious dining table, and a cozy seating area. The ambiance is inviting and perfect for family gatherings, entertaining, and relaxed evenings at home.
Enjoy hearty breakfasts and lingering dinners at the spacious dining table, surrounded by the warmth of an open-concept kitchen.
A warmly lit kitchen with granite countertops, wood cabinetry, stainless steel appliances, and a large window. Decorative wall art adds character, while the generous counter space suggests an environment ideal for meal preparation, casual family brunches, or hosting holiday feasts.
Create culinary masterpieces or savor locally roasted coffee in a kitchen that blends style with function.

Private Retreats & Family Nooks

Features

  • • King-bedded primary suite
  • • Secondary king suite
  • • Bunk room with twin-over-full beds
  • • Premium bedding
  • • Blackout shades/drapes
  • • Spa-quality toiletries
  • • Portable crib
  • • Board games
  • • Bedrooms provide privacy from main living areas

At day’s end, discover spaces designed for restorative sleep and quiet moments apart. The three spacious bedrooms—including a luxurious king-bedded primary suite, a secondary king suite, and a playful bunk room with twin-over-full beds—promise restful nights for every guest. Thoughtful touches like premium bedding, blackout shades, and spa-quality toiletries turn each room into a sanctuary. The bunk room with its board games and cozy nooks is a haven for kids, while couples and friends enjoy privacy and comfort. Families with young children will appreciate the portable crib, blackout drapes, and peaceful ambiance.

A tranquil king-size bedroom featuring a large, plush bed adorned with premium bedding, flanked by nightstands and lamps. The room is bathed in natural light from expansive windows, and blackout shades ensure restful sleep. The serene decor and cozy atmosphere make it an ideal sanctuary for couples or guests seeking privacy and comfort.
Elegant king suite with premium bedding and natural light—your private sanctuary for restful nights.
A family-friendly bunk room featuring twin-over-full bunk beds, cozy decorative pillows, and a floor lamp creating a welcoming nook. Sunlight streams through the window, illuminating comfortable spaces ideal for play, reading, or sleepovers. The layout invites both relaxation and fun for kids or families.
Playful bunk room with cozy nooks—perfect for memorable sleepovers and quiet playtime.
A serene bedroom scene with a comfortable bed, soft linens, elegant nightstands, warm lamps, and a window letting in gentle morning light. The uncluttered design and tranquil color palette enhance the sense of peaceful retreat and privacy.
Tranquil bedroom retreat with soft linens and morning light for ultimate relaxation.

Adventure Launch Pad

Features

  • • Garage storage for outdoor gear and bikes
  • • Keyless entry
  • • Fast WiFi
  • • Mudroom
  • • Laundry area
  • • Garage and mudroom adjacent to main entry
  • • Laundry area accessible from mudroom

Every day is an invitation to adventure, with complimentary curated activities—like snowmobiling, white water rafting, and more—either nearby or a short drive away. The garage provides secure storage for outdoor gear and bikes, making it effortless to transition from mountain exploits to relaxing evenings back at home. Keyless entry and fast WiFi add convenience, while the mudroom and laundry area ensure you’re ready for whatever Colorado throws your way. Whether you’re drying ski gear, prepping for a day at the Rec Center, or grabbing your packs for Rocky Mountain National Park, this home is your private basecamp with all the perks of a luxury resort.

A spacious garage featuring a large garage door, concrete floor, and a ping pong table. The open floor area offers ample space for storing outdoor gear, bikes, and adventure equipment, while the presence of the ping pong table hints at recreational possibilities beyond storage.
Spacious garage with secure storage for all your outdoor adventure gear and bikes.
A practical laundry and mudroom area featuring a modern washing machine, wooden bench, and hooks for organizing coats or gear. The space is tidy, welcoming, and clearly designed for managing the aftermath of outdoor exploits—keeping things clean and organized.
Functional mudroom and laundry area—ideal for drying ski gear and prepping for your next day outdoors.

Explore the Area

This bright, energetic indoor pool scene features children splashing down waterslides, a colorful mural in the background, and families enjoying time together in the water. The environment is lively and inviting, perfectly capturing communal recreation and the fun of the Grand Park Rec Center.
Kids and families soak up the fun at the Grand Park Rec Center’s vibrant pool and waterslide area.
An outdoor panorama bustling with activity: families kayak on a sparkling lake, children giggle down a water slide, hot air balloons float overhead, and groups bike and fish in a natural setting. Multiple generations are engaged in various adventures, all set against a stunning backdrop.
Endless outdoor adventures await – from kayaking and biking to fishing and family water fun, there’s something for every age.
A snow-dusted mountain landscape with a ski lift rising among the trees, inviting guests to explore thrilling winter sports. The sky is clear, and the setting is alive with anticipation for skiing and snowboarding at Winter Park Resort.
Hit the slopes at Winter Park Resort—just minutes away for unforgettable skiing and snow adventures.

Family Fun & Recreation: Adventures for All Ages

Perfect for families and multi-generational groups, this villa places you at the heart of Winter Park's family-friendly excitement. Just minutes from your door, explore the Grand Park Rec Center—with pools, waterslide, climbing wall, and playground—offering hours of fun regardless of the season. Stroll over to The Foundry for bowling, movies, and brick oven pizza nights, or enjoy board games and movie streaming with the kids in your spacious living area. In winter, let everyone experience the thrill of skiing or snow tubing at Winter Park Resort, just 5 minutes away via the local lift bus. With family-focused enhancements like a portable crib and booster chair, plus curated complimentary adventures each day, your stay is seamless and memorable for guests of all ages.

This lively exterior collage captures a family enjoying ice cream, a group rafting down a river, a couple toasting with wine glasses, people skiing and snowboarding, golfing, and horseback riding—all set against beautiful outdoor backdrops. The composite action shots evoke a sense of excitement and variety in mountain activities available year-round.
From exhilarating river rafting to snowy slopes and horseback rides, adventure is always just around the corner.
A scenic mountain village setting with colorful autumn trees, charming wooden houses, a winding road, and distant mountain peaks. The environment feels inviting for walking, biking, or simply soaking in the beauty of the Rockies.
Explore charming mountain roads and vibrant fall foliage just steps from your villa.
A collage of joyful winter moments: people snow tubing down a slope, sled dogs pulling a sled, snowmobiles zipping through snowy scenery, gathering around a fire pit, children learning to ski, and ice skates ready for use. The composite emphasizes group fun and the exhilaration of mountain sports.
Unleash your spirit with snow tubing, snowmobiling, and après-ski gatherings—winter wonders await.

Adventure Awaits: Mountain Sports & Outdoor Thrills

For adventure seekers and outdoor enthusiasts, your villa is a gateway to thrilling experiences. In winter, take advantage of curated snowmobile adventures or hit the slopes at Winter Park Resort. Warmer months invite you to white water raft, mountain bike, or hike scenic trails in Rocky Mountain National Park and Grand Lake, both within a short drive. Secure storage for your bikes and gear, combined with the comfort of luxury accommodations, means you can recharge in style after a day of exploring. Plus, with curated complimentary activities and equipment rentals included in your stay, you'll have everything you need for unforgettable mountain adventures—just steps from your door.

This image features a steaming hot tub set on a wooden deck surrounded by vibrant autumn foliage. The scene is serene, with inviting water reflecting the colors of the season, offering a sense of luxury and relaxation in a natural mountain setting.
Unwind in your private hot tub surrounded by stunning mountain foliage—a perfect retreat after a day of adventure.
A lively exterior shot of Winter Park's Cooper Creek Square, featuring the distinctive sign, festive lights, a wine shop, and a sculpture of a horse. The atmosphere is vibrant, suggesting nearby shopping, dining, and entertainment options just moments from the villa.
Enjoy upscale shopping, dining, and nightlife steps away at Winter Park’s Cooper Creek Square.
A spacious wooden deck overlooks colorful foliage, with architectural details of the villa visible and ample space for gatherings or peaceful relaxation outdoors. The welcoming mood hints at both privacy and the opportunity to enjoy scenic views from the home.
Take in breathtaking mountain views or host gatherings on your villa’s inviting deck.

Luxury Living with Premier Access & Scenic Views

Experience a convenient blend of privacy, space, and home comforts with exclusive resort-style perks. Enjoy the villa's chef's kitchen, private hot tub, contemporary mountain decor, and spa-grade toiletries for indulgent relaxation. Take in mountain and ski run views from your patio or living room, then head out for upscale shopping, dining, and nightlife in downtown Winter Park—only two minutes away. As a guest, you'll benefit from direct booking savings, complimentary curated adventures, and the convenience of being minutes from both the action and tranquil luxury. Whether unwinding after a day of adventure or gathering with friends for a gourmet meal, this home offers high-end amenities and exceptional value.

This exterior image features a cozy hot tub surrounded by wooden fencing and red accents on the building. The space is inviting for relaxing after a day of outdoor activities and is complemented by a grill set up for summer cookouts. The area hints at year-round enjoyment, with potential for stargazing on clear nights or warming up after winter adventures.
Unwind in the hot tub under the stars or host vibrant summer cookouts—relaxation awaits in every season.
This tranquil exterior shot shows a wooden deck surrounded by colorful fall foliage and a stone pathway inviting guests to explore the natural beauty. The setting feels peaceful and is perfect for watching sunsets, hosting gatherings, or simply soaking in the changing seasons.
Enjoy the vibrant colors of fall from your private deck—nature’s beauty right at your doorstep.
An outdoor scene featuring brick-paved pathways, string lights overhead, decorative sculptures, and inviting seating areas. People can be seen strolling, dining, and shopping, evoking a festive downtown Winter Park atmosphere.
Stroll through festive downtown streets, alive with dining, shopping, and local events year-round.

Seasonal Highlights: Experience Winter Park Year-Round

Winter Park's offerings shift with the seasons—and so does your adventure. In winter, the resort comes alive with skiing, snowboarding, and festive village activities. Spring and fall offer quieter, scenic escapes with fewer crowds; while some resort amenities pause during these times, downtown Winter Park remains vibrant with shops, dining, and local events. Summer is perfect for white water rafting, mountain biking, hiking, and exploring nearby lakes and national parks. No matter when you visit, your stay includes exclusive access to a curated selection of top activities—complimentary and tailored just for you—so you can enjoy memorable experiences throughout the year.

Property Amenities All Essentials Included

Facilities & Security

Self Check-in/Check-out

Outdoor Space: Balcony, Patio

Free Parking: Garage

Comfort & Lifestyle

Hair Dryer

Ice-maker

High Chair

Library

Tennis Courts

Onsite Concierge

Dishwasher

Toaster

Clothes Washing Machine

Clothes Dryer

Stove

BBQ Grill

Home Gym

Pool: Community, Heated, Indoor

Hot Tub

Cable TV

Sauna

TV

Laundry Basics: Clothes Dryer, Ironing Board & Iron, Clothes Washing Machine

Oven

EV Charging

Standard Essentials

This property includes a full set of standard essentials (such as towels, bed linens, basic cooking and cleaning supplies).

Ready to Book Your Stay?

Ready for adventure and relaxation in one unforgettable stay? Book your Winter Park villa now and unlock curated experiences, family-friendly comforts, and exclusive perks—year-round.

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Cancellation Policy: Standard

Cancelation Policy

You can cancel this Vacay and get a Full refund up to 14 days prior to arrival

Important Information

Check-in and Check-out Procedures

  • Self check-in/check-out available with door pad for keyless secure entry (24 hour check-in)

Property Access

  • Door pad for keyless secure entry
  • Garage parking for 2 cars

Policies and Rules

  • No smoking allowed.
  • Minimum age: 25 years.
  • Children allowed.
  • No events allowed.
  • No pets allowed (maxPets: 0)
  • Maximum occupancy: 10 guests.

Parking Information

  • Garage parking for 2 cars
  • There is parking for a max of 3 vehicles at the property.

Utilities and Amenities Access

  • Free wireless high-speed internet
  • Most properties in the Winter Park area do not have A/C due to the cooler climate.
  • Towels and bed linens provided.
  • Clothes washing machine and dryer available.
  • Dishwasher and cooking basics provided.
  • Stove, oven, toaster, and ice-maker available.
  • Climate control present.
  • Balcony and patio outdoor spaces.
  • Access to community, indoor, and heated pool.
  • Hot tub and sauna available.
  • Tennis courts and onsite concierge available.
  • High chair for children available.
  • Library accessible.

Fees and Payments

  • No reservation fees by booking direct.

Safety and Emergency Information

  • Smoke alarm and carbon monoxide detector present.
  • STR License #022316

Other Critical Details

  • The resort base closes during the off seasons in the spring and fall, but the downtown area remains open year round.