House holiday rentals in Winter Park

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Top-rated house rentals in Winter Park

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

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Top guest favourite
An open-concept living area features a modern sectional sofa and minimalist coffee tables, with large windows framing views of the surrounding mountains and forest. The kitchen, equipped with sleek cabinetry and appliances, is visible in the background, creating a bright and spacious atmosphere.
Home in Fraser
5 out of 5 average rating, 18 reviews

Devil's Thumb - Modern Mountain Retreat

Discover refined mountain living at our luxe mountain-modern architect-designed 2-bedroom, 2-bath home in Devil’s Thumb Ranch, Tabernash, CO. Savor stunning, unobstructed Continental Divide views from a private 2-acre retreat. Relax in stylish rooms with upscale finishes, explore nearby skiing, hiking, golfing, and dining. Enjoy mountain biking, X-Country skiing, fishing, and more outdoor adventures. Comfort, seclusion, and year-round outdoor activities await you at your exclusive Airbnb escape.

Top guest favourite
A mountain home featuring a large deck and expansive windows that showcase the surrounding nature. The stone chimney adds a rustic touch to the exterior, while the driveway is bordered by a wooden fence. The structure is complemented by a well-maintained landscape.
Home in Winter Park
4.98 out of 5 average rating, 121 reviews

5 Acres, Hot Tub w/Mountain Views, Sledding Hill!

Beautiful mountain home with panoramic mountain views, located on 5 private acres. Home sleeps 14 and features 5 bedrooms and 3 newly renovated baths, along with a recently remodeled kitchen with granite counters and a magnificent wood-burning fireplace. Relax in the hot tub under the stars after a day of skiing or hiking. Park and store your gear in the 4-car garage. Our retreat is only two miles from downtown Fraser and 12 minutes to Winter Park ski area. *Please note: We do not allow events.

Top guest favourite
A person sits comfortably in an Adirondack chair on a deck, enjoying a scenic view of rolling green mountains. A small table nearby holds glasses of red wine and an assortment of fruits, creating a peaceful setting in nature.
Home in Fraser
5 out of 5 average rating, 34 reviews

Modern Mountain Home with Epic Views and Hot Tub

Beautiful 4 bedroom home for 12 guests in the Rendezvous community - near Winter Park Resort, Devils Thumb and Snow Mountain Ranches, Grand Lake and and Rocky Mountain National Park. Groomed hiking and biking trails, a stocked fishing pond, and the Fraser River run right through our neighborhood. Come experience a true Colorado Rockies vacation with epic mountain views, professionally designed interior and outdoor spaces, and amenities the entire family will enjoy: A custom designed fire pit,

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, 166 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
Home in Winter Park
5 out of 5 average rating, 81 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!

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
4.97 out of 5 average rating, 72 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
An inviting dining area features a large wooden table surrounded by black chairs, illuminated by a modern light fixture. A cozy living space is accented by a stone fireplace, wooden beams, and expansive windows showcasing natural light and forest views.
Home in Fraser
4.93 out of 5 average rating, 117 reviews

Winter Park 4 BR Mountain House w/ Private Hot Tub

Bring the whole family to this stunning mountain home which boasts two spacious living rooms, a fully stocked kitchen, and 4 cozy bedrooms with 3.5 baths. Step outside to relax on the covered patio, balcony, or soak in the outdoor 7-person hot tub under the stars! Adventure awaits with downhill skiing, hiking, biking, and a plethora of local restaurants, shops, and parks to explore. Experience the magic of the mountains in this Super Host property, where unforgettable memories are made!

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, 141 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
Home in Fraser
4.94 out of 5 average rating, 112 reviews

Peaceful Mountain Retreat & Clubhouse Access

Your mountain get away close to conveniences and activities with access to shared club hot tub. Located on a quiet street. 1/2 of a duplex on a 3/4 acre lot. Heated garage to keep you warm. A spacious entryway for gear, and parking for three cars. All beds, bedding and couches are new. Crib and high chair available. Large deck. 1.3 miles to Safeway 1.5 miles to restaurants and breweries in Fraser 3.5 miles to town of Winter Park 6 miles to Winter Park Resort Permit STR21-00011

Top 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, 215 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

Top guest favourite
A spacious living area features large windows that offer panoramic views of the mountain valley. A comfortable sectional sofa rests on a vibrantly patterned area rug. Natural light fills the room, highlighting the wooden beams and stone tile flooring.
Home in Granby
4.97 out of 5 average rating, 120 reviews

Winter Park & Grand Lake Home! Views! Hot Tub!

Escape to an inviting Mountain Home! With stunning mountain valley views, a luxurious hot tub, and endless entertainment options like vintage arcade games and shuffleboard, this spacious retreat is perfect for families and groups of friends. The expansive kitchen/dining area is ideal for cooking and gathering, and the five tastefully decorated bedrooms provide ample space and comfort. Plus, pets are welcome for a fee. Create lasting memories at this beautiful mountain getaway!

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, 157 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.

Popular amenities for house rentals in Winter Park

When is the best time to visit Winter Park?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$414 SGD$393 SGD$396 SGD$390 SGD$334 SGD$390 SGD$357 SGD$281 SGD$263 SGD$310 SGD$316 SGD$406 SGD
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Quick stats about house rentals in Winter Park

  • Total holiday rentals

    Explore 300 holiday rentals in Winter Park

  • Nightly prices starting at

    Winter Park holiday rentals start at $104 SGD per night before taxes and fees

  • Verified guest reviews

    Over 5,570 verified reviews to help you choose

  • Family-friendly holiday rentals

    290 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 90 rentals that welcome pets

  • Holiday rentals with a pool

    180 properties feature pools

  • Rentals with dedicated workspaces

    250 properties have a dedicated workspace

  • Wifi availability

    300 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!

Destinations to explore

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