Downtown Winter Park Condo with Pool, Hot Tub & Free Adventures

Welcome to a rare mountain escape in downtown Winter Park—where the comfort and privacy of a spacious three-bedroom, three-bath condo meets exclusive resort-style amenities. Perfectly positioned for families, adventure seekers, pet owners, and groups, this pet-friendly home inside Trailhead Lodge Resort offers heated pool and hot tub access, a vibrant clubhouse, and curated complimentary adventures. Enjoy flexible sleeping arrangements for up to 10 guests, gather in the open-concept living spaces, and take advantage of hotel-style perks like optional concierge services—all just steps from dining, shopping, and year-round entertainment. Please note: Some amenities and activities are seasonal, but downtown excitement awaits in every season.

10 10 guests
3 3 bedrooms
3 3 bathrooms
Winter Park Winter Park, Colorado
A spacious, inviting living room featuring plush sofas gathered around a glowing stone fireplace, a large TV mounted above the mantle, and a sleek coffee table—perfect for gathering with family and friends. Floor-to-ceiling windows offer breathtaking sunset views, while warm lighting and mountain-inspired décor create a cozy, welcoming retreat.
Unwind by the crackling fire as golden sunsets pour through panoramic windows—your cozy mountain sanctuary for unforgettable moments with family and friends awaits in Winter Park.

Spacious 3-bedroom/3-bath condo sleeping up to 10 · Exclusive complimentary daily adventures · Central downtown Winter Park location with walkable access to dining and entertainment · Private clubhouse with pool, hot tub, and gym · Pet-friendly with explicit policy and restrictions

The Social Heart: Gather, Feast, and Connect

Features

  • • Open-concept layout
  • • Gas fireplace
  • • HD smart TV
  • • Chef’s kitchen with premium appliances
  • • Kids’ dinnerware
  • • Board games
  • • Flows into dining area and kitchen
  • • Central gathering space for all guests

Step into the expansive open-concept living, dining, and kitchen area—the vibrant heart of your mountain retreat. Here, families and groups can gather around the beautiful gas fireplace, share laughter over board games on plush seating, or stream favorite shows on the HD smart TV. The chef’s kitchen, fully equipped with premium appliances, kids’ dinnerware, locally roasted coffee, and ample space, is an invitation for everyone to cook, snack, and socialize together. The adjacent dining area easily accommodates group meals or game nights, and large windows invite mountain light, blending the warmth of home with contemporary luxury. Whether planning adventures or unwinding after a day on the slopes, this communal space offers togetherness and comfort in every season.

This image features a spacious and inviting dining area set with plates and cutlery, bar stools at the kitchen counter, premium kitchen appliances, and a window that lets in natural mountain light. The scene evokes a sense of togetherness, with ample space for group meals, cooking, and social activities.
Gather around the dining table for memorable meals and laughter-filled game nights in a sunlit, open space.
This warm living room scene highlights a cozy gas fireplace, a comfortable sofa with decorative pillows, a coffee table, and an HD smart TV. The setup invites relaxation, socializing, and family entertainment, mirroring the atmosphere described in the section content.
Unwind by the glowing fireplace, enjoy movie nights, or catch up with friends in the heart of the home.
This perspective centers on the kitchen island with bar stools, stainless steel appliances, and decorative touches like hanging light fixtures and plates. The welcoming mood suggests both culinary creativity and connection, ideal for cooking together, snacks, or casual conversation.
Create delicious meals, bake cookies, or sip morning coffee in a chef-inspired kitchen designed for connection.

Private Retreats: Rest, Recharge, and Dream

Features

  • • Two king bedrooms
  • • One queen bedroom
  • • Flexible bunk room (converted from a study)
  • • Blackout shades
  • • 5-star hotel quality toiletries
  • • Pack and play
  • • Booster seat
  • • Sleeping quarters connect to bathrooms and main living area

Find sanctuary across the home’s thoughtfully designed sleeping quarters—each a tranquil haven after a day of adventure. Two king bedrooms, one queen bedroom, and a flexible bunk room (converted from a study) ensure every guest, from couples to kids, enjoys privacy and comfort. Luxurious linens, blackout shades, and premium bath amenities—including 5-star hotel quality toiletries—promise restful nights, while the pack and play, booster seat, and flexible sleeping arrangements make it uniquely family-friendly. Three well-appointed bathrooms with luxury toiletries provide both convenience and pampering. Whether curling up for a peaceful sleep or enjoying a quiet moment, these retreats are crafted for deep relaxation.

A king-sized bed with a wooden headboard sits beside a nightstand and lamp. Soft, sheer curtains filter natural light into the serene bedroom, creating an inviting space for rest and relaxation.
King bedroom with soft natural light and plush bedding, designed for ultimate comfort.
A queen bed topped with a purple throw blanket stands before a mirrored wardrobe and is flanked by nightstands with lamps. Decorative wall plates add character to this calm, cozy bedroom.
Cozy queen bedroom with elegant accents and inviting atmosphere for peaceful nights.
A set of bunk beds with decorative pillows and a nightstand create a playful yet restful sleeping space, ideal for kids or flexible arrangements. The room’s soft colors and textures add to its welcoming ambiance.
Flexible bunk room perfect for kids or extra guests, featuring cozy beds and playful decor.
A modern bathroom with a glass shower enclosure, double sink vanity, large mirrors, and sleek lighting. The space feels refreshing and spa-like, ideal for self-care and pampering.
Spa-inspired bathroom with luxury amenities and bright, serene atmosphere.

Resort-Style Escape: Exclusive Amenities at Your Doorstep

Features

  • • Heated outdoor pool
  • • Hot tub
  • • Game room
  • • Theatre lounge
  • • Entertainment kitchen (large group-use kitchen in clubhouse)
  • • Gym
  • • Firepit
  • • Elevator access
  • • Pet-friendly policies
  • • Clubhouse located steps from the condo
  • • Easy access from main entry

Experience the rare blend of private home intimacy and exclusive resort indulgence. Just steps away, Trailhead Lodge’s private clubhouse offers a heated outdoor pool, hot tub, game room, theatre lounge, a large group-use kitchen in the clubhouse (entertainment kitchen), gym, and a cozy firepit—perfect for unwinding, playing, or gathering as a group. With elevator access and pet-friendly policies (see restrictions), even practicalities are handled with luxurious ease. Enjoy the freedom of year-round relaxation, knowing that while some amenities vary by season, the downtown’s shops, entertainment, and dining are always at your fingertips. This is resort living made personal.

This image features a heated outdoor swimming pool surrounded by lounge chairs and a wooden clubhouse building, with lush trees in the background. The setting is inviting for swimming, sunbathing, and socializing, offering a relaxed, resort-style atmosphere.
Heated outdoor pool with scenic lounge area—perfect for relaxation and social gatherings.
A cozy lounge area inside the clubhouse, anchored by a large television and a warm fireplace, with plush sofas and a window view. The space is ideal for movie nights, group gatherings, or simply relaxing in comfort.
Cozy theatre lounge with fireplace—ideal for movie nights or casual hangouts.
An inviting clubhouse kitchen and dining area, with ample seating and large windows providing natural light. The setting is designed for group dining, entertaining, and community events.
Spacious clubhouse kitchen and dining area for group meals and celebrations.
A modern gym with various exercise equipment, large windows for natural light, and a television. The space feels open and energizing, perfect for personal fitness routines or group workouts.
State-of-the-art gym—stay active without leaving the comfort of home.

Adventure Concierge: Curated Experiences from Your Mountain Home

Features

  • • Exclusive complimentary daily adventures
  • • Optional concierge services: grocery shopping, in-home massage, private chef, equipment fittings
  • • Concierge services available in-home and at the resort

Unlock the region’s best with exclusive, complimentary daily adventures—ranging from thrilling snowmobile rides in winter to white water rafting in summer. Plan your outings with ease, knowing you can return to the comfort and privacy of your luxury home. Optional concierge services—grocery shopping, in-home massage, private chef, and custom equipment fittings—bring five-star hotel perks directly to your living room. While some activities are seasonal and must be reserved in advance (see details), the unbeatable combination of curated local experiences and personalized hospitality sets this property apart. Here, every day is an invitation to create lasting memories in both comfort and style.

A vibrant interior collage showcasing guests participating in a range of adventurous activities: white-water rafting, wine tasting, golfing, skiing, snow tubing, horseback riding, and enjoying ice cream. The setting conveys energy and fun, with active individuals and families immersing themselves in both summer and winter experiences.
Experience every adventure—from white-water rafting to skiing—right from your mountain home.
An inviting interior scene with a spa treatment in progress, delicious food delivery, family cooking together, and festive holiday decorations. Skiing gear and a family enjoying quality time underscore both relaxation and activity. The composition conveys five-star hotel perks and personalized hospitality available in-home.
Enjoy luxurious in-home spa services, gourmet meals, and festive memories—all tailored to your comfort.
A cozy living room setting featuring a stylish sofa with plush pillows, a glowing fireplace, large windows letting in natural light, and a chic coffee table. The atmosphere is one of relaxation, comfort, and togetherness—ideal for unwinding after an adventurous day.
Return to the comfort and privacy of a luxurious home after your daily adventures.

Explore the Area

The image features the iconic Cooper Creek Square sign, a wine shop, and inviting outdoor seating areas, all illuminated by decorative lights. The scene is lively and welcoming, capturing the energetic spirit of downtown Winter Park.
Stroll through Cooper Creek Square—Winter Park’s hub for unique shopping, dining, and vibrant events.
A dynamic outdoor amphitheater with a distinctive curved roof and stonework stands ready for community gatherings, concerts, and events. The stage area is the focal point, promising exciting performances and shared experiences.
Catch live concerts and family-friendly events at Hideaway Park Amphitheater—right across the street.
This exterior shot showcases the welcoming entrance to Trailhead Lodge Resort, featuring stone pillars, wooden accents, red chairs, and a landscaped pathway. People are gathering and relaxing outdoors, suggesting an inviting, community-oriented atmosphere.
Enjoy the inviting ambiance of Trailhead Lodge—where leisure and adventure meet at your doorstep.

Downtown Winter Park at Your Doorstep

Step outside and immerse yourself in the vibrant heart of downtown Winter Park. Whether you love exploring unique mountain shops, savoring family-friendly restaurants, or joining in on lively events and concerts at Hideaway Park Amphitheater—just across the street—this location places you at the center of it all. With Trailhead Lodge Resort’s exclusive clubhouse (game room, movie theater, pool, and more) just steps away, families, groups, and value-focused travelers can seamlessly blend leisure time at home with endless urban excitement. Plus, enjoy easy access to the FREE resort shuttle for quick trips to Winter Park Resort’s lifts, tubing, and village fun.

Location Advantage: No need to drive—walk everywhere! Perfect for groups wanting to split up for different activities or reunite for shared experiences in the evenings.

A lively and colorful outdoor scene featuring people partaking in a wide variety of adventure activities such as white-water rafting, mountain biking, kayaking, horseback riding, tubing, and sliding down a water slide. The image bursts with vibrant landscapes and shows both families and groups enjoying active pursuits under clear skies, with colorful hot air balloons accenting the festive, adventurous atmosphere.
Experience the thrill of the Rockies—rafting, biking, and more, all included in your stay!
A montage of winter fun, with scenes of people snow tubing, dog sledding, snowmobiling, skiing, snowboarding, and ice skating. The image includes happy families, children, and groups enjoying snowy landscapes, along with cozy touches like a fire and huskies, amplifying the sense of shared winter excitement and warmth.
Winter wonderland: snowmobiling, skiing, sledding, and more—adventures await every guest.
A panoramic view of snow-covered mountains with ski lift gondolas gliding between frosted trees. The scene offers a sense of awe and tranquility, inviting guests to imagine themselves experiencing the majestic landscape firsthand, whether skiing, snowboarding, or simply taking in the views.
Take in breathtaking Rocky Mountain vistas before heading out on your next adventure.

Rocky Mountain Thrills: Complimentary Adventures All Year

Unlock the best of Winter Park with exclusive, complimentary adventures curated just for Winter Park Escapes guests! Eligible for one complimentary activity per day, subject to availability and advance reservation. From heart-pounding snowmobile tours, skiing, and snowboarding in winter, to exhilarating white water rafting and mountain biking in summer, each season brings new opportunities to explore—on us. Simply reserve your spot in advance and enjoy local experiences made possible only for our guests. After a day outdoors, relax in your private condo with luxury comforts or wind down in the resort hot tub and heated pool.

Note: Complimentary activities are seasonal and subject to availability. The list of current adventures is always up to date on our website, ensuring you get the most out of your stay!

This image features the condo complex's stone entrance sign, wooden balconies, and lush surrounding greenery. The inviting facade and visible balconies indicate a welcoming environment with direct access to nature and outdoor adventures.
Welcoming entrance with easy access to scenic trails and outdoor fun for the whole family.
An exterior shot showing a communal fire pit, seating area, grill, and building facade surrounded by greenery. The setup is ideal for group gatherings, outdoor dining, and evening relaxation under the stars.
Gather around the fire pit for s'mores and stories after a day of adventure.
A lively interior scene from the nearby Rec Center featuring colorful water slides, swimming pools, and playful murals, with children and families enjoying water play.
Make a splash at the Rec Center’s kid-friendly pools and waterslides—just steps from your door.

Family Fun, Inside and Out

This condo is designed with families in mind! Take advantage of the oversized floor plan, kid-friendly amenities (including a bunk room and children’s dinnerware), and a great collection of board games for cozy nights in. When you’re ready to venture out, stroll along the nearby trail system for scenic hikes and bike rides, or head to the Rec Center for swimming, a climbing wall, and a playground. The Foundry next door offers bowling and movies—a perfect family night out. Retreat to your spacious home for a homemade meal in the chef’s kitchen or a board game tournament by the fireplace.

Property Highlight: The flexible sleeping arrangements comfortably host large or multi-generational families, making bonding easy and evenings restful.

This exterior scene features comfortable lounge chairs and a small round table set on a patio surrounded by lush greenery. Wooden pillars frame the outdoor area, creating an inviting space ideal for relaxing, socializing, or enjoying the sunrise or sunset. The tranquil ambiance suggests a direct connection to nature and outdoor recreation.
Relax in comfort on the inviting lounge chairs, surrounded by mountain greenery just steps from your door.
An exterior scene filled with twinkling string lights and festive decorative stars, featuring stone fountains, outdoor seating, and a brick walkway. The atmosphere is joyful and celebratory, suggesting a vibrant community perfect for strolls, dining, or attending local events with your dog.
Enjoy festive evenings and strolls through the vibrant, pet-friendly local scene.
A balcony scene with cozy seating overlooking surrounding buildings and an open outdoor view. The atmosphere is casual and comfortable, suggesting a spot to relax with your pet while taking in the sights and sounds of the mountain community.
Take in the mountain air from your private balcony after a day of adventure with your pups.

Pet-Friendly Mountain Adventures

Bring your furry companions on your mountain getaway! This luxury condo welcomes up to two dogs (nightly pet fee applies; see pet policy for details), so you and your pups can enjoy walking trails just outside your door and the nearby open spaces of Winter Park. Many local patios and parks are pet-friendly, making it easy to include your dog in your vacation fun. After exploring, return to your comfortable home base knowing your four-legged friends are just as welcome as you are!

Please note: Pet stays are limited to two dogs (max) and are not permitted for visits longer than 14 days. A nightly fee applies. Contact us with any questions on our clear pet policy.

A welcoming outdoor balcony featuring comfortable seating, a dining table, and sweeping mountain views in the distance. The area is well-appointed for relaxation or social gatherings, with the natural scenery providing a resort-like atmosphere.
Unwind on the private balcony with breathtaking mountain views—perfect for morning coffee, sunset dining, or simply soaking up the serene surroundings.
A cozy living room complete with a striking stone fireplace, large panoramic windows, a plush leather sofa, and a wooden coffee table. The space feels warm, stylish, and is ideal for socializing or quiet relaxation.
Gather by the stone fireplace for intimate evenings or lively conversations in the heart of your home-away-from-home.
A vibrant game room featuring a pool table, large windows that flood the space with light, and a modern fireplace. The atmosphere is lively and social, ideal for unwinding or friendly competition after a day of adventure.
Challenge friends to a game of pool or relax fireside in this stylish, sunlit entertainment space.

Relaxation & Rejuvenation: Private Home, Resort Perks

Indulge in the luxury of a private home while enjoying the perks of an upscale resort. Unwind with a soak in the heated outdoor pool or hot tub, catch a movie in the clubhouse theater, or treat yourself to an in-room massage arranged by our concierge. For foodies, book a private chef or explore downtown’s gourmet offerings. Whether you seek wellness, leisure, or a little pampering after a day of adventure, this property’s blend of home comfort and hotel-style services is renowned for its combination of comfort and amenities in Winter Park.

Insider Tip: Our team can help arrange grocery delivery, private dining, or custom adventure planning—just ask!

This image captures an inviting entryway featuring a console table, lamp, artwork, and a bench—elements that evoke the experience of arriving at or departing for seasonal adventures in Winter Park. The welcoming decor hints at a cozy and hospitable atmosphere, which aligns with the section's focus on year-round enjoyment and exploration.
Welcome home to Winter Park—your starting point for mountain adventures and festive downtown experiences.
This space shows metal lockers, an elevator, and a staircase, signifying the practical side of adventure—storing equipment, coming back from the slopes, or heading out to explore. The image feels dynamic and purposeful, suited to active, seasonal lifestyles.
Gear up or wind down—secure equipment and easy access set the stage for every season's adventures.

Seasonal Highlights: Winter and Summer in Winter Park

Winter brings direct access to world-class skiing, snowboarding, and snowmobiling, with nearby lifts and shuttle service to the Winter Park Resort base. As the snow melts, summer opens up endless mountain biking, hiking, and white water rafting. Local festivals, concerts, and farmer’s markets in downtown keep the fun going year-round. Please note: Some resort base amenities and free adventure offerings are seasonal—check for current schedules. But no matter the season, downtown Winter Park’s dining, shopping, and entertainment are always open for you to enjoy.

Property Amenities All Essentials Included

Facilities & Security

Elevator

Self Check-in/Check-out

Handicap Accessible

Outdoor Space: Balcony, Patio

Free Parking

Comfort & Lifestyle

Hair Dryer

Ice-maker

High Chair

Library

Tennis Courts

Onsite Concierge

Dishwasher

Toaster

Pool Table

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

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?

Book your stay today!

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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

  • Keyless secure entry with 24-hour self check-in and check-out.

Property Access

  • Keyless entry provided.
  • Elevator access available.

Policies and Rules

  • No smoking allowed.
  • Minimum age: 25 years.
  • Children allowed.
  • No events allowed.

Pet Policy

  • This property allows dogs. Maximum pets allowed: 99.
  • A pet fee may apply. Please check with management for current rates and policies.
  • Reservations with pets may be subject to specific restrictions. Please verify before booking.

Fees and Payments

  • No security deposit or reservation fee required.

Parking Information

  • The unit includes free parking.

Utilities and Amenities Access

  • Free high-speed Wi-Fi.
  • Towels and bed linens provided.
  • Climate control available.
  • Hair dryer available.
  • Cooking basics, stove, oven, dishwasher, toaster, and ice-maker provided.
  • Clothes washing machine and dryer available.
  • High chair and onsite concierge available.
  • Library, pool table, tennis courts, community heated indoor pool, hot tub, and sauna available.
  • Smoke alarm and carbon monoxide detector provided.

Safety and Emergency Information

  • STR license #022148.

Additional Critical Details

  • Many properties in Winter Park do not have A/C due to the cooler climate.
  • The resort base closes during spring and fall off-seasons. Dates vary depending on snow conditions. The downtown area remains open year-round.