Holiday houses in Winter Park

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Top-rated holiday rentals in Winter Park

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Top Guest favourite
A private hot tub is located on the patio, providing views of the living space through large glass doors. The interior features an open layout with a cozy fireplace and a TV visible on the wall. Modern furnishings create a welcoming environment.
Townhouse in Winter park
4.98 out of 5 average rating, 129 reviews

Modern Cabin w/ Hot Tub & Garage - Minutes to Mtn

2BR townhome with a loft in a woodsy neighborhood in Winter Park/Fraser. Want a relaxing scenic place to sit by the fire or enjoy Grand County's outdoor adventures? Come stay and enjoy this townhome with access to free shuttle transportation during the winter. Both bedrooms include King beds. The loft includes a daybed that expands to a king bed and the sofa pulls out to a bed. PRIVATE 7 PERSON HOT TUB on patio. Propane Grill, easy access to hiking/biking trails, restaurants, stores, bars, etc.

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, 186 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 circular hot tub is positioned within a fenced area, surrounded by snow-covered ground. The three-story building, featuring a mix of stone and siding, stands in the background under a clear blue sky. Balconies and sliding glass doors are visible on the structure.
Apartment in Winter Park
4.95 out of 5 average rating, 149 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, 279 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, 275 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
A modern stand-alone unit features a covered cedar deck with two dark wooden chairs facing an inviting entryway. Pathways lead through landscaped areas, with grassy surroundings and trees partially framing the view. An outdoor sauna is visible in the background.
Home in Fraser
4.98 out of 5 average rating, 102 reviews

Modern Downtown Home w/ Private Sauna on Bus Line

Enjoy a sanctuary in the heart of charming downtown Fraser—complete with a private outdoor sauna! Tucked among aspens yet just steps from the Fraser train/bus station, this modern home offers a rare blend of seclusion, convenience, and character (the train rumbles by across the street). Leave your car at home and enjoy restaurants, bars, coffee, grocery, and frequent transit to Winter Park all within an easy walk. Stocked with everything you need to feel at home, it’s the perfect basecamp.

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, 495 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 peaceful outdoor view showcases still waters bordered by lush greenery and distant mountains under a bright blue sky. Bicycles are parked on the balcony, emphasizing accessibility to outdoor activities and trails nearby.
Condo in Fraser
4.97 out of 5 average rating, 128 reviews

Walk to Restaurants! Work Remotely!

Summer fun is right around the corner. Hike, bike and fish from the front door! Don’t miss this spacious 1 BR Fraser condo perfectly located for your spring and summer adventures in Grand County. You are just a short walk from the grocery store, restaurants, breweries and the Fraser River and Trail. You are a .8 mile walk from the train station which offers daily Amtrak service and weekend Ski train service in the winter. You are also steps away from the free Lift shuttle service.

Top Guest favourite
A welcoming outdoor entryway features a covered porch with colorful hanging flower baskets. Two chairs are positioned next to a small table, inviting relaxation. A decorative rug adorns the area, complementing the wooden structure and surrounding greenery.
Guest suite in Fraser
4.97 out of 5 average rating, 482 reviews

Madge’s Studio 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 summer activities. In addition, we are 45 minutes from Rocky Mountain National Park and the lakes of Grand Lake. After enjoying a perfect Colorado day, come back to your spacious room for a drink on your private patio to think about what restaurant to enjoy.

Top Guest favourite
A bright living room features large windows that invite natural light and offers views of the outdoors. A spacious leather sectional sofa is positioned around a wooden coffee table, with a cozy area rug beneath. A modern fireplace and wall-mounted TV complete the inviting space.
Home in Winter Park
4.99 out of 5 average rating, 148 reviews

Luxury Mtn Cabin/Free Shuttle/ Views/Garage

Escape to Mountain Flower Cabin located in the Rendezvous community just a short walk to downtown Winter Park and a 4 mile shuttle ride (free) to Winter Park Ski Resort. Our 3BR cabin is well appointed with custom furniture, modern amenities, and breathtaking mtn views. Nestled within the Rendezvous Trail System, alongside the Fraser River, you'll find miles of hiking, biking, fishing and cross country skiing right outside your door. The free shuttle to WP is steps from the cabin.

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, 106 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
Home in Fraser
4.95 out of 5 average rating, 165 reviews

Cozy Cabin Retreat • Hot Tub, Fireplace, Views

Beautiful, spacious, and cozy cabin perfectly located for year-round mountain adventures. Minutes from Winter Park Ski Resort, downtown Winter Park, and Fraser, and under an hour to Rocky Mountain National Park and Grand Lake. Enjoy stunning Byers Peak views from the patio, with easy access to hiking, biking, and Nordic ski trails. Comfortably accommodating multiple adults or two families, this home offers all-season access to Grand County’s outdoor recreation and scenic beauty.

Popular amenities for Winter Park holiday rentals

When is the best time to visit Winter Park?

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Avg. price$457 NZD$452 NZD$464 NZD$296 NZD$278 NZD$294 NZD$338 NZD$301 NZD$303 NZD$313 NZD$354 NZD$506 NZD
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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.

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 $123 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

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  3. Colorado
  4. Grand County
  5. Winter Park