Vacation rentals in Winter Park

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Top-rated vacation rentals in Winter Park

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Top guest favorite
An open living area showcases a black leather sectional couch arranged around a circular wooden coffee table adorned with greenery. Wooden accents highlight the walls, while soft lighting illuminates the adjacent kitchen and dining space visible in the background.
Townhouse in Winter Park
4.98 out of 5 average rating, 184 reviews

Modern/Rustic 2-bedroom Townhouse + Bonus Loft

Newly renovated modern/rustic three-story A-Frame townhome on the free shuttle route. Small and cozy, this 2 bedroom (+ lofted bed) can comfortably accommodate 5, but it should be noted that there's only 1 full bathroom! The location is perfect: it's quiet and serene while only being minutes from downtown Winter Park and two miles from the WP Resort. Vasquez Road is .4 miles from the front door to access everything the National Forest has to offer (hiking, snowshoe excursions, mountain biking)

Guest favorite
The welcoming living area showcases a spacious sectional sofa adorned with a colorful throw. A stone accent wall complements the large flat-screen smart TV. Natural light enters through expansive windows, illuminating the area, while a modern counter separates the kitchen from the living space.
Condo in Winter Park
4.94 out of 5 average rating, 153 reviews

Cozy mountain retreat in downtown Winter Park

Lovingly remodeled Hi Country Haus 1 bedroom 1 bathroom condo central to downtown Winter Park. Use our Tiny Mountain Retreat as a launchpad to all the local access Winter Park has to offer or as a space for rejuvenation in this beautiful mountain town. Incredible access to local trail running, mountain biking, backpacking, fly-fishing, hiking and skiing. Grand Lake and Rocky Mountain National Park are easily and often visited from our spot as well. WP Short-term rental registration #019404

Top guest favorite
The fully equipped kitchen features wood cabinetry, modern appliances, and a large island with seating for four. A dining area with a circular table and four chairs is positioned nearby. Warm lighting is provided by a decorative pendant fixture, enhancing the cozy ambiance.
Condo in Winter Park
4.93 out of 5 average rating, 277 reviews

Top Floor Condo Steps From Free Shuttle w/Hot Tub

Two bedroom, Two bath, top floor condo with three private balconies. Our fully equipped kitchen comes complete with all the amenities you need to prepare your favorite meals, and we provide complimentary toiletries for your convenience. 15 minute walk to main street bars and restaurants and on the free ski shuttle line to the Mountain or Main Street. Take advantage of our free parking in front of the building and unwind after a long day on the slopes or trails in the community outdoor hot tub.

Guest favorite
A modern studio is presented, featuring a well-equipped kitchen with bar stools at the counter. Two armchairs sit on a patterned area rug, and a spacious bed is visible in the foreground. The design incorporates neutral tones and textured wall tiles.
Condo in Winter Park
4.88 out of 5 average rating, 249 reviews

Homebase Snowblaze

Enjoy the magic of the Fraser River Valley and charm of downtown Winter Park from our well-equipped, completely remodeled studio. Only an hour and thirty minute drive from Denver International Airport. Walking distance to Winter Park's Main St. lined with shops and dining and a quick 5 minute drive to the world class slopes of Winter Park resort. Take advantage of the free "Lift" bus, with a stop right out front of the building and a ride to the resort in less than 5 minutes. WP STR # 009036.

Top guest favorite
The exterior of a charming European-style home is displayed, featuring multiple windows with green shutters. A balcony adorned with vibrant flower boxes complements the rustic architecture. Lush greenery surrounds the property, enhancing its inviting appearance against a clear blue sky.
Guest suite in Winter Park
4.98 out of 5 average rating, 492 reviews

Charming Suite in Old Town Winter Park

Charming European suite steps away from a major ski resort. Located in the heart of Old Town Winter Park this beautiful European Country home is a welcoming retreat for mountain visitors. OUR LARGE PRIVATE SUITE IS IN THE LOWER LEVEL OF OUR HOME, complete with separate bedroom, kitchenette, hot tub, bathroom/shower & FREE PARKING! Take a 10-15 minute walk or short bus ride to the base of the Winter Park Resort to experience incredible skiing and boarding at any of the Resort's Territories.

Top guest favorite
A modern living area is highlighted by a comfortable sectional sofa and a square glass coffee table. Floor-to-ceiling windows showcase scenic mountain views, while bright light fills the room. The open layout includes a sleek television mounted on the wall and a glimpse of the dining area.
Apartment in Winter Park
4.97 out of 5 average rating, 102 reviews

Luxury Winter Park Studio*PrivHotTub*Majestic View

Brand New Studio styled in HIP MOUNTAIN CONTEMPORARY in EXCLUSIVE Leland Creek! Perched amongst the aspen trees with spectacular sunset views,you'll never want to leave your own private Hot Tub and Deck!Floor to ceiling windows with stunning mountain views,Room+Board furniture and rustic ski vibe fill the home with a Contemporary Chic style.Private Entrance.Good Pets are welcome.10miles to Granby.18 miles to Grand Lake+Rocky Mountain National Park.DenverInternational airport 1.5 HR.

Guest favorite
A modern mountain chalet is nestled among snow-covered trees, showcasing its striking dark exterior against the winter landscape. The property is elevated on a hillside, offering panoramic views, while a winding driveway leads up to the home.
Cabin in Tabernash
4.91 out of 5 average rating, 231 reviews

Mountain Getaway - Hot Tub & Sauna. Dogs welcome!

Escape to our luxury Colorado mountain retreat with stunning Continental Divide views! Comfortably sleeps 8. Features a chef's kitchen, indoor 6-person hot tub & sauna, and a wood-burning fireplace. Family-friendly with a bunk room and travel crib. Just 15 mins to Winter Park Ski Resort & 30 mins to Rocky Mountain National Park. Perfect for adventure and relaxation. We love dogs and they’re welcome in our home! Please make sure to add them to the booking so we know they’re coming.

Guest favorite
The spacious living area features a striking wood ceiling and a decorative stone fireplace. A comfortable sectional sofa faces a mounted television, while a dining table accommodates six people. Large windows allow natural light to illuminate the space, creating a welcoming environment.
Townhouse in Winter Park
4.92 out of 5 average rating, 170 reviews

Spacious Mountain Townhome | Private Hot Tub

Prepare for a mountain retreat in this beautiful 3 bed/3 bath townhome + private indoor hot tub. Downtown Winter Park just 3 blocks off main street where you will find many shops, restaurants, bars, city parks and entertainment for the entire family. The perfect fit for families/groups looking for space to spread out, a stocked kitchen to cook in, and a hot tub to unwind in at the end of an amazing day. Only 5 minutes from Winter Park Resort and near the free bus line!

Guest favorite
The living area features a spacious leather sectional sofa arranged around a coffee table, creating an inviting space. A stone fireplace serves as a focal point, while large windows allow natural light to fill the room. A television is positioned within a wooden console.
Townhouse in Winter Park
4.9 out of 5 average rating, 225 reviews

Beautiful Townhome in Downtown Winter Park!

(Winter Park short term rental no. 004831) Townhouse in the heart of downtown Winter Park is perfect for families and large groups! This home is steps away from Hideaway Park and the ski bus. With beds for 10 people, private bathrooms & a garage/driveways that can fit 4 cars, this home is ideal for groups. The kitchen is fully stocked with everything you need. For young children, we have everything from a high chair to a stroller to toys to a pack and play.

Top guest favorite
Guest suite in Fraser
4.97 out of 5 average rating, 480 reviews

Fall in to winter at Madge’s. Pets welcome!

Whether it be play time or quiet time (or both!), we offer our guests (and pets) the comfort of a large studio and yard at the end of a dead end street. You have a beautiful mountain setting with easy access to all your favorite winter activities; Fraser Valley has them in spades! After enjoying a perfect Colorado winter day, come back to your spacious room for a drink by your cozy fireplace to think about what restaurant to enjoy to cap a wonderful day.

Guest favorite
The exterior of the condo complex is visible, showcasing multiple levels adorned with windows. Snow blankets the landscape, while a heated outdoor area features seating and a hot tub. Mountain views provide a scenic backdrop, emphasizing the peaceful surroundings.
Condo in Winter Park
4.87 out of 5 average rating, 205 reviews

One Bdrm Condo Ski In / Ski Out, Hot Tub, Fire Pit

Located in the Winter Park Village, walking distance to The Gondola this condo has it all! The bedroom features a King bed with a memory foam pull out Queen in the living area. Complete Kitchen, full size fridge, dishwasher, large bathroom, and private covered patio with views of the Mountain. Walking distance to shopping, restaurants, & activities! One of only a handful of units with direct outdoor access. UPDATE: New hot tub is OPEN! Permit #009238

Guest favorite
A tastefully arranged sleeping area features a dark green accent wall and a modern bed with neutral bedding. A stylish nightstand with a small plant and clock is positioned beside the bed, illuminated by a sleek wall-mounted lamp.
Condo in Winter Park
4.89 out of 5 average rating, 220 reviews

Ski In/Ski Out - Modern Cozy Condo in Winter Park

Leone’s Den | A Boutique Mountain Retreat at the Base of Winter Park Resort Step into refined alpine comfort at Leone’s Den, an elegant studio just steps from the slopes. Located across from the Village Base, enjoy easy access to dining, shopping, and après-ski, then retreat to a warm space with a cozy fireplace and elevated finishes. Relax in Winter Park’s largest hot tub and return to plush linens and beautiful mountain and village views.

Popular amenities for Winter Park vacation rentals

When is the best time to visit Winter Park?

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Frequently Asked Questions

  • What are the best places to stay in Winter Park?

    Winter Park has inviting neighborhoods near ski slopes, scenic mountain views, and easy trail access. Many visitors choose to stay around the resort area or in town for walkable dining, shopping, and outdoor activities.

  • What are the best things to do in Winter Park with kids?

    Families frequently enjoy sledding, snow tubing, and exploring playgrounds in the winter. In warmer seasons, mini-golf, adventure parks, and guided nature walks are often suggested for younger travelers.

  • What are some of the best things to do in Winter Park?

    Explore the slopes at Winter Park Resort, hike scenic trails, and experience mountain biking or fishing in alpine lakes. Art galleries, local shops, and seasonal festivals add variety throughout the year.

  • How is the weather in Winter Park?

    Winter Park has cold, snowy winters with temperatures ranging from 11 to 36°F (-11 to 2°C), while summer afternoons warm to 62–68°F (17–20°C). Spring and fall are cooler and may bring brief rain or scattered snow.

  • When is the best time to visit Winter Park?

    Winter Park is frequently suggested in winter for skiing and snowboarding, while summer attracts mountain bikers, hikers, and festival goers. Spring and fall bring quieter trails and crisp mountain air.

  • What are the best places to visit in Winter Park?

    Travelers often explore Winter Park Resort, stroll through Hideaway Park, and wander the town’s local art galleries. Seasonal farmers markets and community spaces are also popular gathering spots.

  • What are some hiking trails in Winter Park?

    Winter Park has several frequently suggested hiking trails, including the Fraser River Trail, Jim Creek Trail, and trails around Berthoud Pass. Alpine forests, wildflowers, and broad mountain views make hiking a favorite activity.

  • What are some family activities we can do in Winter Park?

    Families can explore scenic bike paths, visit adventure parks, and try out nearby wildlife watching areas. Guided tours, fishing experiences, and seasonal community events bring people together year round.

  • What are some of the best day trip ideas from Winter Park?

    Day trips from Winter Park often include exploring mountain lakes, small towns with historic main streets, or natural hot springs tucked in scenic valleys. Outdoor parks and wildlife areas around the region are also popular.

  • Are there any pet friendly accommodations available in Winter Park?

    Winter Park has pet-friendly vacation rentals in neighborhoods near the resort, main street, and park areas. Many hosts welcome dogs, and outdoor trails make it easy to explore with your companion.

  • What are some local tips for visiting Winter Park?

    Layer clothing for changing mountain weather, and bring sunscreen for high-altitude sun. Exploring early in the day is often recommended for quieter trails and wildlife sightings.

  • What is Winter Park known for?

    Winter Park is known for its ski resort, mountain biking terrain, and vibrant outdoor recreation. Seasonal festivals, art spaces, and alpine scenery make it a favorite destination for adventurers.

  • What are the best hidden gems to explore in Winter Park?

    Wander quiet trails near local creeks, discover tucked-away parks, or seek out small art galleries and coffee shops just off the main street. Lesser-known fishing spots and forested picnic areas reward curious explorers.

  • What are the best foods to try in Winter Park?

    Try locally inspired dishes such as hearty chili, Rocky Mountain trout, and fresh baked pies in area cafes. In winter, warming stews and hot cocoa are frequently suggested favorites.

  • What should I bring for a trip to Winter Park?

    Bring layers for temperature changes, sturdy shoes for outdoor activities, and sunscreen for higher elevations. In winter, pack gloves, a warm hat, and waterproof gear for snow sports.

  • What is the nightlife in Winter Park like?

    Winter Park has lively bars, casual lounges, and venues hosting local music around the town center. Après-ski gatherings and group-friendly restaurants create a relaxed evening atmosphere.

  • What are the most popular events or festivals in Winter Park?

    Winter Park has recurring music festivals, mountain bike races, and art fairs, often anchored around summer weekends and winter holidays. Seasonal celebrations bring live entertainment and local flavor to community spaces.

  • Are there family friendly vacation rentals in Winter Park?

    Winter Park has a range of family-friendly vacation rentals near town, ski lifts, and recreation areas. Many spaces include additional amenities and flexible layouts for groups traveling with children.

All about Winter Park

This small mountain town consistently earns high praise from winter sports enthusiasts for its more than 3,000 acres of well-groomed slopes and powder stashes spread over seven separate ski areas. Its location in the Rocky Mountains positions it for more than 300 inches of prime powder each year; the runs are designed for skiers of all levels, making Winter Park the perfect place to go with the whole family or a group of friends. Even if skiing isn’t at the top of your list, other winter activities like snowshoeing, tubing, and snowcat tours provide plenty of options. Plus a new scenic gondola lets you take in the panoramic views.

What are the top things to do in Winter Park?

Winter Park Resort

Winter Park Resort is the ideal basecamp for adventure, and features a wide range of activities year-round. There are many ways to experience the great outdoors here. A tubing park and bumper car course are popular with kids, while Nordic skiing and snowshoeing provide a slower-paced experience. When you’re through breaking a sweat, there are more than a dozen shops and restaurants to visit.

Winter Park Gondola

The Winter Park Gondola is the easiest and fastest way to access views of the Colorado Rockies in any season, whisking you to 11,000 feet elevation. The ride up offers a bird’s-eye view of ski runs and tree canopies. At the summit, you’re greeted by panoramic views of the Continental Divide and Fraser Valley, as well as access to hiking trails, lookouts, and a variety of ski runs.

James Peak Wilderness

Less than an hour’s drive from Winter Park is one of Colorado’s most impressive and underrated landscapes. James Peak Wilderness is located on the eastern side of the Continental Divide, and encompasses 17,000 acres. More than 20 miles of trails and streams meander through this alpine and subalpine ecosystem, including stands of willow, spruce, and Douglas firs.

Quick stats about vacation rentals in Winter Park

  • Total vacation rentals

    Explore 1,550 vacation rentals in Winter Park

  • Nightly prices starting at

    Winter Park vacation rentals start at ﺩ.ﺇ257 per night before taxes and fees

  • Verified guest reviews

    Over 45,440 verified reviews to help you choose

  • Family-friendly vacation rentals

    1,190 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 270 rentals that welcome pets

  • Vacation rentals with a pool

    580 properties feature pools

  • Rentals with dedicated workspaces

    910 properties have a dedicated workspace

  • Wi-Fi availability

    1,540 of Winter Park vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Self check-in, Gym, and BBQ grill across Winter Park rentals

  • 4.8 Average rating

    Winter Park stays are highly rated by guests—averaging 4.8 out of 5!

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