Holiday houses in Winter Park

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Top-rated holiday rentals in Winter Park

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Top Guest favourite
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, 185 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)

Top Guest favourite
A modern kitchen space is highlighted by a central island with seating for four. Sleek cabinetry in soft colors complements stainless steel appliances, including a refrigerator and a range hood. Pendant lights provide illumination above the island, enhancing the inviting atmosphere.
Apartment in Winter Park
4.95 out of 5 average rating, 148 reviews

Tipsy Fox @ Downtown Winter Park Near the Slopes!

Welcome to the perfect Winter Park getaway! Located in downtown, this cozy one-bed, one-bath condo is just steps away from Hideaway Park and its year-round free events. With 3 queen beds, including a sleeper sofa and a Murphy bed, it comfortably sleeps 6 guests. Enjoy the heated garage and ski locker for your vehicle and snow gear. After outdoor activities, unwind in the hot tub, gather around the fire-pit, or relax on the balcony. Conveniently close to food, slopes, tubing hill, and amenities

Guest favourite
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.

Top Guest favourite
The modern mountain home is showcased against a backdrop of snow-covered terrain and distant mountain peaks. Its angled roof and contemporary design blend seamlessly with the natural surroundings. Large windows reflect the serene landscape, while surrounding trees add to the tranquil winter setting.
Cabin in Grand County
4.96 out of 5 average rating, 273 reviews

Scandinavian-Inspired Escape: Modern Cabin w/ Spa

Escape to our Modern Mountain Home in Grand County, Colorado, where luxury meets wilderness! Nestled amidst majestic mountains, this Scandinavian-inspired retreat offers the perfect blend of rustic charm and contemporary comfort.  Wake up to breathtaking views, with hiking, biking, and skiing right outside your door.  Highlights: • Panoramic mountain views • Close to Winter Park & RMNP • Scandinavian-inspired design • Wood-burning fireplace • Private hot tub Grand County Permit #106884

Top Guest favourite
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, 494 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 favourite
A spacious living area is shown, featuring a large sectional couch adorned with various decorative pillows. A coffee table sits at its center, and two armchairs are positioned nearby. Natural light enters through sliding glass doors, providing a view of the outside snow-covered landscape.
Condo in Winter Park
4.84 out of 5 average rating, 237 reviews

Main Street Luxury - Hot Tub + Trails

You'll feel right at home at the hearth of this updated condo. You'll be on the slopes in 2 bus stops with pickup just outside. On Main Street, across from Cooper Creek and the Rendezvous Event Center, the town awaits. Host family style feasts with the fully equipped kitchen and dine up to nine. Relax in the hot tubs, on the huge couch by the big screen digital cable TV with streaming services, on the deck and in the hot tubs. Decadent Cal King bed in master. Ski lockers by the elevator.

Top Guest favourite
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, 104 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 favourite
The exterior of the log cabin is showcased against a clear blue sky, surrounded by vibrant autumn foliage. A gravel driveway leads to the entrance, while a spacious yard reflects the natural beauty of the mountain landscape, adorned with tall trees and colorful foliage.
Cabin in Tabernash
4.92 out of 5 average rating, 179 reviews

Cozy Log Cabin Getaway ~ 20 Min to Winter Park

Come stay in our cozy log cabin in the mountains! Beautifully made 1,300 sqft log home with wood burning fireplace, huge private yard, loft and 3 bedrooms (sleeps up to 6). This cozy cabin has 1 private acre with lots of wildlife, hiking and riding trails. High speed internet included if you wish to work or watch streaming services during your stay. 20 minutes from Winter Park Resort and 10 minutes from Granby Ranch while still feeling tucked away in your own mountain getaway!

Guest favourite
An outdoor heated pool is featured alongside two hot tubs, surrounded by a scenic landscape of snow-covered trees and mountains. The area is paved with a spacious deck for relaxation, with clear skies above enhancing the serene atmosphere of the retreat.
Condo in Winter Park
4.94 out of 5 average rating, 188 reviews

Ski-in/Ski-out, Luxury amenities +Free parking

Discover the perfect mountain retreat! Enjoy seamless ski-in/ski-out access, a first-floor location, and unwind in the indoor/outdoor heated pool and new hot tubs. Stay fit in our on-site fitness center, park hassle-free, and explore with a free local shuttle at your doorstep. With custom queen and bunk murphy beds, this cozy escape offers comfort and convenience. Your mountain getaway awaits – embrace the charm, relax, and make unforgettable memories!

Top Guest favourite
The living space features a modern kitchen with stainless steel appliances and a sleek bar area. A leather sofa and armchair surround a round coffee table, creating a comfortable seating arrangement. A colorful artwork hangs on the wall, complemented by stylish lighting fixtures.
Condo in Winter Park
4.99 out of 5 average rating, 107 reviews

Winter Park Condo on the River: Walk to Downtown!

Welcome to Riverview where you will enjoy privacy and beautiful views of the Fraser River from this stylish retreat. This one-bedroom condo is equipped with a pillow soft queen-size bed, queen-size sofa sleeper, full kitchen, bathroom, electric fireplace, & patio. Located directly across from a ski shuttle stop and a short walk to Winter Park's Main St. lined with shops and dining.

Top Guest favourite
Guest suite in Fraser
4.92 out of 5 average rating, 675 reviews

Winter has arrived!

Cute studio with everything you need. The bed is a murphy bed, very comfortable. Comfy couch with ottoman. Kitchenette, bathroom. This property is very simple. Close to trails to trails and the town of Winter Park and Fraser. You might even see some wild life! Leave your worries behind and get in the zone! Rise with the sun, Sleep with the stars, Always create fireworks!

Guest favourite
A cozy living area features a wooden dining table surrounded by sturdy chairs, with a ceiling fan overhead. Large windows allow natural light to flood the space, providing views of the mountains. A decorative stone wall adds warmth, complemented by comfortable seating.
Townhouse in Fraser
4.96 out of 5 average rating, 170 reviews

Mountain View Getaway

Kick up your feet, relax and take in the stunning mountain views in our spacious, sunlit home. It is recently remodeled, so everything is in great shape. Great for kids but also only a 3 minute walk to 2 breweries, new distillery, and several restaurants.

Popular amenities for Winter Park holiday rentals

When is the best time to visit Winter Park?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$446 NZD$441 NZD$453 NZD$289 NZD$272 NZD$287 NZD$330 NZD$294 NZD$296 NZD$306 NZD$345 NZD$494 NZD
Avg. temp-7°C-7°C-3°C-1°C4°C9°C13°C12°C8°C2°C-3°C-7°C

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.

Quick stats about holiday rentals in Winter Park

  • Total holiday rentals

    Explore 1,550 holiday rentals in Winter Park

  • Nightly prices starting at

    Winter Park holiday rentals start at $120 NZD per night before taxes and fees

  • Verified guest reviews

    Over 45,440 verified reviews to help you choose

  • Family-friendly holiday rentals

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

  • Pet-friendly accommodation

    Find 270 rentals that welcome pets

  • Holiday 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 holiday 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!

Destinations to explore

  1. Airbnb
  2. United States
  3. Colorado
  4. Grand County
  5. Winter Park