House holiday rentals in Winter Park

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Top-rated house rentals in Winter Park

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Guest favourite
A secluded chalet is surrounded by towering trees and located next to a gently flowing river. The dark wood structure features large windows and a spacious deck, inviting a connection with nature and providing serene views of the natural landscape.
Home in Winter Park
4.96 out of 5 average rating, 168 reviews

Winter Park Creekside Chalet with Hot Tub

Experience nature in this scenic 4-bedroom, 3-bathroom chalet that is secluded amongst the trees and river yet close to everything. Choose having your morning beverage nestled in front of the fireplace or in a hot tub overlooking the river. The property is perfectly situated with downtown just 1 mile away or Winter Park Resort within a 10 minute drive and located on the Lift bus route too. Or, stay around the house with access to beautiful hiking and mountain biking trails just 1 block away!

Top guest favourite
The family room features floor-to-ceiling windows that frame views of lush pine trees and the Fraser River. A cozy seating arrangement for eight includes two large sofas and a white accent chair, complemented by a neutral area rug and a dark coffee table at the center.
Home in Winter Park
5 out of 5 average rating, 14 reviews

*NEW* Luxe Waterfront Condo in Winter Park

Headwaters Hideaway, a 1,500+ sq ft Winter Park condo, boasting 180* waterfront, mountain & forest views. Just a 5-minute drive to Winter Park Resort and 100 feet to large ponds and the Fraser River trail. Enjoy a private patio, dual master suites, and room for up to 10 guests. Cook up a storm in our fully stocked kitchen, or take a 5-min walk to 10+ restaurants. In the summer, 5-Star Golf & Lake Granby are just a short drive away. This Hideaway is perfect for winter skiing or summertime events.

Top guest favourite
Home in Winter Park
5 out of 5 average rating, 88 reviews

Cozy Modern Cabin w/ Hot Tub - Minutes to Ski Area

@cabin.57 is an Ideal Winter Park vacation home for families or small group of friends looking for the perfect mountain getaway. You'll feel right at home the moment you step inside the home's beautiful interior, boasting impressive high-quality furnishings and decadent mountain touches, including a gas fireplace and custom double wide sliding door that opens from living room to the hot tub patio area. Walk to town and enjoy all the Winter Park restaurants and shops. Steps to Lift Bus stop!

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, 85 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.

Guest favourite
A welcoming living room features a comfortable couch adorned with patterned cushions. A modern electric fireplace is below a wall-mounted television. Natural light filters through sliding glass doors, which open to a view of the outdoors, framed by yellow curtains.
Home in Fraser
4.93 out of 5 average rating, 83 reviews

Private Hot Tub, Garage + EV Charger, On Bus Line!

Welcome to your mountain home! Relax in your private 6 person hot tub on your back patio, or have your morning coffee from the patio while taking in the mountain views. Only a few minutes walk to the shuttle line, be at Winter Park in no time at all! After a day on the slopes, relax in front of the fireplace or outdoor fire pit. The primary bedroom has an attached private bathroom, while the spacious guest room features a tub + shower. Have an EV? Charge for free in your heated garage!

Top guest favourite
A spacious living area features large windows allowing ample natural light. A large leather sectional is positioned near a gas fireplace, complemented by two modern chairs. A flat-screen TV is mounted on the wall opposite, and a coffee table sits on a decorative rug.
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.

Guest favourite
The outdoor space showcases a stone fire pit surrounded by natural rock seating. The patio is supported by sturdy stone columns, with comfortable seating arranged under a large covered area. A hot tub is visible nearby, and lush landscaping enhances the setting.
Home in Granby
4.98 out of 5 average rating, 223 reviews

Wildhorse Chalet at Grand Elk - With Hot Tub!

This 5-bedroom (4 bedrooms + loft), ranch is located in the Grand Elk community of Granby, CO. The home offers over 2600sf of contemporary mountain decor. The home was designed to maximize both indoor and outdoor living. Whether you're looking to ski/snowboard at Granby Ranch and/or Winter Park, paddle-board at Grand Lake, golf at Grand Elk, or if you're just seeking a relaxing weekend away with friends and family, we're confident your stay will be one to remember. Permit #004096

Guest favourite
An open-concept living area showcases a comfortable sofa paired with a round dining table. A modern fireplace is accentuated by a dark wall, while large windows invite natural light and offer views of the balcony. Sleek appliances are present in the fully equipped kitchen.
Home in Fraser
4.95 out of 5 average rating, 76 reviews

Mountain Cozy | New w/ Hot Tub

Relax in this cozy, new build mountain retreat, ideally located minutes from world renowned Winter Park Ski Resort. This new build 2-bed, 2-bath + bunk space condo includes a private hot tub, fully equipped kitchen, smart TVs, balcony w/ mtn views, washer/dryer, and heated garage. This condo is in a perfect location, just 2 minutes from Fraser grocery/restaurants/bars, 8 minutes to Winter Park, 20 mins to Granby Ranch, and just minutes to endless hiking and biking trails.

Top guest favourite
A spacious wooden cabin features large glass windows showcasing mountain views and an outdoor deck. The deck includes an umbrella and railing made of timber. The surrounding landscape is neatly landscaped with grass and decorative plants.
Home in Fraser
4.92 out of 5 average rating, 100 reviews

Luxury Home w/Hot Tub & Winter Park Ski Mtn Views!

This luxurious 6-bed, 5.5-bath Fraser vacation rental house can host up to 14 guests with ease throughout 4,341 square feet! This spectacular residence includes countless upgrades, such as a private hot tub, in-floor radiant heated floors on all levels including the garage, remote control blinds, and granite countertops. With a massive interior, spectacular mountain views from the deck, and the free shuttle stop less than 1 block away, experience mountain living in style!

Top guest favourite
A spacious cabin structure is set against a clear blue sky, surrounded by snow-covered ground. A partially covered porch features several outdoor chairs, and a two-car garage is visible beneath the home. A pathway leads to the entrance, emphasizing the inviting atmosphere.
Home in Fraser
4.95 out of 5 average rating, 160 reviews

Spacious Cabin Retreat w/ Hot Tub Near It All

Beautiful, spacious and cozy cabin conveniently located with easy access to Winter Park Ski Resort, downtown Winter Park, Fraser and less than 1hr drive to Rocky Mountain National Park and Grand Lake for year round mountain adventures! Enjoy stunning views of Byers Peak from the patio with easy access to hiking, biking or Nordic ski trails. This home boasts all season access to all Grand County has to offer while comfortably accommodating multiple adults or 2 families.

Top guest favourite
Home in Fraser
5 out of 5 average rating, 35 reviews

Red Wolf Lodge - Private Hot Tub - Mountain Views

Brand new home in beautiful and tranquil Fraser. 3 bedroom, 2 bathroom, private hot tub. 15 minutes to Winter Park Resort, 30 minutes to Granby and Grand Lakes, 40 minutes to the RMNP entrance at Grand Lake. Comfortably furnished and well appointed with everything you need to enjoy your vacation while feeling right at home. Enjoy this quiet, modern, and cozy mountain retreat just a quick drive from amenities in Fraser such as restaurants, breweries, groceries

Top guest favourite
A modern townhome is depicted, featuring a combination of wood and blue accents. The structure includes large balconies and garages at the base, with a landscaped area of rocks and grass surrounding the entrance. The silhouette of nearby buildings is visible against a clear sky.
Home in Fraser
5 out of 5 average rating, 21 reviews

Relax & Play – Mountain Stay

Escape to this beautiful 3-bedroom, 3-bathroom townhome in Fraser, CO, offering breathtaking mountain views and modern comforts. Relax in the 7-person hot tub, cozy up by the fireplace, or enjoy a game on the foosball table. The kids’ room features a 3-bed bunk and hangout space. Conveniently located on the free bus route with easy access to Winter Park Resort, dining, and shopping. Includes heated garage, washer/dryer, and more for a perfect getaway!

Popular amenities for house rentals in Winter Park

When is the best time to visit Winter Park?

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Avg. price$410 SGD$389 SGD$392 SGD$387 SGD$331 SGD$387 SGD$353 SGD$278 SGD$260 SGD$307 SGD$313 SGD$402 SGD
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Quick stats about house rentals in Winter Park

  • Total holiday rentals

    Explore 330 holiday rentals in Winter Park

  • Nightly prices starting at

    Winter Park holiday rentals start at $129 SGD per night before taxes and fees

  • Verified guest reviews

    Over 5,730 verified reviews to help you choose

  • Family-friendly holiday rentals

    320 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 90 rentals that welcome pets

  • Holiday rentals with a pool

    140 properties feature pools

  • Rentals with dedicated workspaces

    270 properties have a dedicated workspace

  • Wifi availability

    330 of Winter Park holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool 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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