House holiday rentals in Winter Park

Find and book unique houses on Airbnb

Quick stats about house rentals in Winter Park

  • Total holiday rentals

    Explore 360 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 6,680 verified reviews to help you choose

  • Family-friendly holiday rentals

    350 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

    290 properties have a dedicated workspace

  • Wifi availability

    360 of Winter Park holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Winter Park rentals

  • 4.9 Average rating

    Winter Park stays are highly rated by guests – averaging 4.9 out of 5!

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 Fraser
4.97 out of 5 average rating, 127 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 Winter Park
5.0 out of 5 average rating, 11 reviews

Chateau Louise • Group & Family Friendly • Central

Modern mountain comfort meets unbeatable walkability at this stylish 3BR Winter Park retreat. Stroll to local cafés, restaurants, bars, & boutiques. Unwind in the private hot tub with plush Parachute robes, relax by the fireplace, play records from the curated vinyl collection, or settle in with games and books after a day outdoors. The fully stocked kitchen features a Moccamaster coffee maker, while luxe linens, cozy beds, and elevated bath products create the perfect all-season alpine getaway.

Guest favourite
Home in Fraser
5.0 out of 5 average rating, 10 reviews

Lodge 212 | Brand New LUXE Designer Home + Hot Tub

Welcome to Lodge 212! This brand new mountain retreat blends designer luxury w/ family-friendly comfort. Spacious rooms and endless amenities create the perfect home base for your group. Head to the loft to challenge others to a game of pool while streaming your favorite team, then step outside to soak in the hot tub, toast marshmallows, and soak up the sweeping mountain views. With easy access to skiing, hiking, biking, + fishing, every day is an adventure + every evening a cozy family escape!

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
4.95 out of 5 average rating, 175 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 1 mile away, Winter Park Resort within a 10 minute drive and 75 steps from 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
5.0 out of 5 average rating, 15 reviews

Winter Park Home | Hot Tub Sauna Walk to Downtown

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!

Superhost
Home in Winter Park
4.73 out of 5 average rating, 22 reviews

Chalet Apres | Amazing Location | Hot Tub & Sauna

Stay in the heart of Winter Park on Main Street at Chalet Apres. Walk to all shops, dining, and Hideaway Park, or hop on the ski bus right outside to head to the slopes. This gorgeous townhouse features 2 king bedrooms and a twin, private hot tub and sauna, leg massagers, locked ski storage, ski boot dryer, and the comforts of a hotel with more space and convenience. Located in the new build Arrow community, there will be retail, restaurants and fun events at the amphitheater all year round!

Top guest favourite
Home in Winter Park
4.99 out of 5 average rating, 152 reviews

Pool Access & Mtn View! Luxe WP Cabin, Near Trails

Rendezvous Neighborhood | 1 Mi to Dtwn Bites & Brews | Walk to Fraser River Adventure begins right out your door at this Winter Park vacation rental, where alpine trails and fresh air set the stage for an unforgettable stay. Hike and bike through scenic terrain, or take advantage of Club MeadowRidge amenities just a short drive away. Then return to unwind in a beautiful cabin thoughtfully designed with custom furniture, modern amenities, and epic views. This is mountain living at its best!

Top guest favourite
The open living space features a comfortable gray sofa and two leather armchairs, with a wooden coffee table at the center. Large windows frame views of trees, while a stone fireplace adds warmth. A well-equipped kitchen is visible in the background, complemented by wooden cabinetry.
Home in Winter Park
5.0 out of 5 average rating, 18 reviews

Duplex In town! Views! PrvtHottub,2Cgarage,Sleeps9

BEST location!! In-town duplex has spectacular mountain views from the deck and plenty of space for multiple families, sleeps 9. Easy access to trailheads and the free Lift shuttle from the front door. Private hot tub, 2 living rooms, 3 bedrooms with en suite bathrooms, full size washer and dryer, main level entrance, gas BBQ, and 2 car garage with 220 outlet for EV charging plus free/easy parking next to house. Just 1 mile to Hideaway Park for easy access to restaurants and shopping!

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, 103 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!

Guest favourite
Home in Fraser
4.95 out of 5 average rating, 171 reviews

Spacious Cabin • Family Friendly • Hot Tub • Views

Spacious mountain retreat in Winter Park with sweeping mountain and ski slope views. Minutes to Winter Park Resort, downtown, and Fraser, 30 mins to lakes and under 1hr to Rocky Mountain National Park. Relax in the private hot tub, gather around the fireplace, or enjoy open living with smart TVs, games, heated garage, grill, and outdoor dining. Easy access to hiking, biking and skiing. Comfortably sleeps 10, making it the perfect year-round Colorado getaway for families and groups.

Top guest favourite
A cozy seating area is visible through a large window, showcasing a stunning view of the snow-covered mountains under a soft pink and blue sky. The wooden balcony railing frames the scene, enhancing the connection with nature.
Home in Tabernash
4.98 out of 5 average rating, 106 reviews

Continental Divide Views! New Log Home w/ Hot Tub!

Come enjoy a piece of paradise! Our new log home is the perfect base for your Colorado mountain adventure! You’ll find space for up to ten, with four bedrooms, three bathrooms, two living areas, and a fully stocked kitchen. Located between Winter Park ski and Grand Lake, you can ski, snowboard, visit Rocky Mountain National Park, hike, bike, golf, fish, or boat. At the end of the day, relax in the hot tub or on the wrap-around deck and enjoy unparalleled Continental Divide views.

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, 88 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.

Popular amenities for house rentals in Winter Park

When is the best time to visit Winter Park?

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Avg. price$421 SGD$451 SGD$389 SGD$388 SGD$332 SGD$388 SGD$354 SGD$279 SGD$261 SGD$283 SGD$323 SGD$417 SGD
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