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
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
4.97 out of 5 average rating, 126 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
Home in Fraser
5 out of 5 average rating, 25 reviews

Luxury Mountain Cabin-Views, Hot Tub-10 ppl

Escape to a luxury mountain retreat in Fraser, just minutes from Winter Park—perfect for families and groups. Relax in the private hot tub with stunning mountain views, or challenge friends in the game room. Sleeps 10 comfortably with 4 bedrooms, including a loft and fun bunk room. Skiing, tubing, golf, trails, and endless outdoor adventure. Thoughtfully designed with high-end finishes, a cozy fireplace, and a chef’s kitchen opening to spacious living. Book now for your perfect Colorado getaway!

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, 171 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
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, 105 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.

Superhost
Home in Winter Park
5 out of 5 average rating, 4 reviews

Home Spa Retreat Downtown WP Walk to Shops Dining

Escape to Ramble On, a pet friendly luxury wellness retreat in downtown Winter Park for 10. - Unwind in your private rooftop hot tub & barrel sauna after a day on the slopes, just a 5-min drive or free shuttle away. - This 4-bed mountain-modern home features a theater room, chef's kitchen, and stunning views. - Perfect for families & groups seeking style and adventure, steps from the Fraser River and local shops. - Tap the ❤ in the upper-right corner to add Ramble On to your wishlist!

Guest favourite
A spacious mountain home is showcased with a rustic exterior, featuring wooden siding and a gabled roof. A heart-shaped flower bed made of stone borders the front yard, surrounded by open fields and distant mountain views under a clear blue sky.
Home in Granby
4.92 out of 5 average rating, 113 reviews

Grand Elk Getaway! - Mountain Views & 7 Beds!

Welcome to Beautiful Grand Elk Getaway! Spacious & private mountain home with a modern rustic feel; Tons of natural light, vaulted ceilings & unobstructed 360 mountain views! Our Grand Elk Getaway is ideal for couples or families looking to explore Winter Park, Granby, Grand Lake and RMNP! Perfect Grand County location- 20 minutes to Winter Park, 15 Minutes to Grand Lake & Lake Granby. 5 minutes to Granby Ranch! Bring your Skis, Snowmobiles, Boats, Golf Clubs, Hiking Boots, & Fishing Gear

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
4.9 out of 5 average rating, 31 reviews

Modern Mountain Retreat | 2 Acres | Private Trails

indulge in elevated mountain living at this architect-designed 2BR/2BA retreat set on 2 private acres in the Devil’s Thumb Ranch area. Take in the nobstructed Continental Divide views, explore private trails just outside your door, and unwind by the fire pit beneath a canopy of stars. Ski or snowshoe directly from the home, then return to seclusion, comfort, and style. Planning a photo shoot, intimate dinner party, or special event? Please inquire for approval and applicable event fee.

Guest favourite
A barnwood home is framed by snow-covered trees, featuring a distinct architectural design with multiple gables. Large windows allow for ample natural light, while a stone walkway leads to the welcoming entrance. The two-car garage is visible, showcasing the spacious layout of the property.
Home in Granby
4.92 out of 5 average rating, 174 reviews

Barnwood Beauty @ Grand Elk- Pet Friendly- Hot Tub

Offering a warm welcome to family and friends, Saddle Ridge Lodge touts high-end, family-friendly finishes throughout. Spend the days on the slopes or golf course and spend the evenings soaking in the private hot tub or competing in a game of foosball. The spacious layout is perfect for families and groups with two living rooms, a playroom, gas fireplaces, a high-end kitchen, and a large patio with a grill, egg smoker, and a hot tub. What’s more? Your dog can join in on the fun, too!

Top guest favourite
An illustrated representation of Mountain Flower Cabin features a modern two-story structure set against a mountainous backdrop. Elements such as trees and a bicycle are detailed, along with the sun and stars, conveying a serene connection to nature in Winter Park, Colorado.
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
Home in Fraser
4.94 out of 5 average rating, 108 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, 229 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
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 house rentals in Winter Park

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Quick stats about house rentals in Winter Park

  • Total holiday rentals

    Explore 350 holiday rentals in Winter Park

  • Nightly prices starting at

    Winter Park holiday rentals start at £44 per night before taxes and fees

  • Verified guest reviews

    Over 6,680 verified reviews to help you choose

  • Family-friendly holiday rentals

    340 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 90 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    280 properties have a dedicated workspace

  • Wifi availability

    350 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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  5. Winter Park
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