Holiday houses in Winter Park

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Top-rated holiday rentals in Winter Park

Guests agree: these stays are highly rated for location, cleanliness and more.

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Superhost
The inviting A-frame exterior is framed by surrounding snow-covered trees, showcasing a large raised patio with decorative railings. Warm interior lighting spills through the windows, contrasting with the serene winter landscape.
Cabin in Fraser
4.83 out of 5 average rating, 103 reviews

Charming Rocky Mountain A-Frame

The Woodland A-Frame Retreat is NEWLY RENOVATED as of December 2021. It features a tranquil and private setting tucked amongst the 1 acre lot's aspens and pines. Byer’s Peak mountain views from the front deck. Located on the free shuttle route (the Lyft stop is two houses away!) and a bike ride away from Idlewild Trail system. Open living area with loft, granite countertops, stainless steel appliances, washer/dryer and a cozy wood stove. Enjoy all the modern comforts with a rustic a-frame charm.

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, 173 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 (+ loft) space 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)

Superhost
The rustic cabin exterior is framed by tall aspen trees and features a wooden door. Bright flower boxes, filled with white and red blooms, add a pop of color in front of the porch area. A grill is positioned nearby on the deck.
Cabin in Winter Park
4.84 out of 5 average rating, 608 reviews

Cozy Cabin in Perfect Location

You've found the perfect cabin for your trip to Winter Park. Cozy, w/a queen bed & a single, pull-out couch. Small kitchen or -on a nice day- grill on back deck near creek. Electric fireplace adds ambiance. Tiny kitchen w/appliances, Keurig &dishes. STEPS away from Cooper Creek Town Square restaurants & Hideaway Park’s concerts. The City of Winter Park has trains going through the town, which adds to the charm. We love pets/dogs! 2 or more dogs require extra $10 per dog one-time cleaning fee.

Top 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, 264 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 favourite
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
4.87 out of 5 average rating, 230 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 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, 474 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, modern home is nestled among tall trees, with a welcoming exterior featuring a combination of rustic and contemporary designs. The garage doors and entryway are clearly visible, with a scenic backdrop of mountains and a blue sky dotted with fluffy clouds.
Townhouse in Fraser
4.99 out of 5 average rating, 122 reviews

Luxury Winter Park Cabin w/Hot Tub & Pet Friendly

The Wildflower is a private luxurious home in Winter Park next to beautiful national forest and less than 5 min to downtown WP for restaurants, shopping, and more! Skiing at Winter Park is 5 min away with hiking and biking out the front door! Come enjoy the private oversized hot tub after a long day of fun or walk to downtown for dinner and shopping. Fully stocked kitchen and pet friendly with a private 2-car garage and high-speed WiFi. 2 master bedrooms and extra living area for the kids!

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
4.83 out of 5 average rating, 222 reviews

Main Street Luxury- Downtown with 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.

Guest favourite
An open living area is featured, presenting a comfortable sectional sofa, a coffee table, and a dining area with bar stools. Natural light fills the space through high windows, illuminating the contemporary artwork on the wall. A kitchen is visible in the background, showcasing wood cabinetry.
Condo in Fraser
4.86 out of 5 average rating, 109 reviews

Mountain Getaway Condo w/ Pool and Hot Tub

Freshly Updated- 2 Bedroom, 1 Bath Meadow Ridge Condo with space for the whole family or your favorite group to enjoy a mountain getaway! Located right on the FREE shuttle route to Winter Park Ski Resort, adventure awaits in every direction from this perfectly located condo. Start hiking or biking right out the front door. Guests have access to all the amenities at Club MeadowRidge, located steps away from the condo. Stay, Play, Relax at our wonderful Mountain Getaway!

Top Guest favourite
Guest suite in Fraser
4.96 out of 5 average rating, 455 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.

Top Guest favourite
A bright living space features a light-colored sofa positioned near a large window, showcasing views of the outdoors. The walls are adorned with warm wood paneling, while a minimalist table sits in front of the sofa. Natural light enhances the cozy atmosphere.
Apartment in Winter Park
4.95 out of 5 average rating, 128 reviews

Calm vibes and a great view at the Alpen Rose

Currently available for weekly and longer rentals. Will review any other requests. Welcome! I'm sharing with you my home away from home. A stay here comes with wonderful views of the Continental Divide and Winter Park Resort. The Lyft (free bus) stops just a few steps from the house. Cook with a view and fully stocked kitchen. The living space has a comfy sofa and wood-burning stove. Molekule air filters & Dyson fan to keep you comfortable.

Guest favourite
The studio accommodates a cozy sleeping area with a queen Murphy bed and a queen pull-out couch. Large windows provide natural light, and rustic wooden accents enhance the interior. A small table and comfortable seating complete the inviting atmosphere.
Condo in Granby
4.85 out of 5 average rating, 200 reviews

Studio~Ski Granby/Winter Park. Pool/Hot Tubs

This 2nd floor studio is located at the Inn at Silvercreek in Granby Ranch. It is 495 sq ft. Inside the studio has been updated and is stylish and cozy. The resort offers many amenities including pool, hot tubs, an arcade, a gym and even a barber shop. The location is about 5 min from the Granby Ski area, 20 min to Grand Lake and 30 min to either RMNP or Winter Park. There is a free “Lift” shuttle to Winter Park during the ski season.

Popular amenities for Winter Park holiday rentals

When is the best time to visit Winter Park?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$457 NZD$452 NZD$464 NZD$296 NZD$278 NZD$294 NZD$329 NZD$343 NZD$313 NZD$301 NZD$320 NZD$476 NZD
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Quick stats about holiday rentals in Winter Park

  • Total holiday rentals

    Explore 1,470 holiday rentals in Winter Park

  • Nightly prices starting at

    Winter Park holiday rentals start at $18 NZD per night before taxes and fees

  • Verified guest reviews

    Over 45,410 verified reviews to help you choose

  • Family-friendly holiday rentals

    1,120 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 250 rentals that welcome pets

  • Holiday rentals with a pool

    580 properties feature pools

  • Rentals with dedicated workspaces

    860 properties have a dedicated workspace

  • Wi-Fi availability

    1,460 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!

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