Ski-in/Ski-out holiday rentals in Winter Park

Find and book unique ski-in/out homes on Airbnb

Quick stats about holiday rentals that are ski-in/out in Winter Park

  • Total holiday rentals

    Explore 390 holiday rentals in Winter Park

  • Nightly prices starting at

    Winter Park holiday rentals start at $90 SGD per night before taxes and fees

  • Verified guest reviews

    Over 9,630 verified reviews to help you choose

  • Family-friendly holiday rentals

    220 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Holiday rentals with a pool

    80 properties feature pools

  • Rentals with dedicated workspaces

    150 properties have a dedicated workspace

  • Wifi availability

    390 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!

Top-rated ski-in/out rentals in Winter Park

Guests agree: these ski-in/out homes are highly rated for location, cleanliness and more.

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Top guest favourite
A warm and inviting open concept living space features a leather couch with decorative pillows facing a dining area and a kitchen. The kitchen showcases wooden cabinetry and stainless steel appliances, while large windows allow natural light to brighten the room.
Home in Fraser
4.94 out of 5 average rating, 104 reviews

Wonderful,Hot tub Steam Shower,1 acre,wifi 600mbps

Lovely house, HOT TUB,1 acre, 2 K beds, Bunk Room T/T & F/F, 2 pullouts -Q/T & 3.5 bathrooms,steam shower, 2 family rooms w/4K HD TV. Walk 3 min. free bus shuttle or drive 6 mile 2 Winter Park. Fully equipped kitchen w/SS appliances,granite,heated 1.5 car garage,WiFi, Apple TV, huge washer & 2 dryers, deck w/gas GRILL,XBOX/games,in floor radiant heat,gas FP,sleds,Pack-n-Play, crib,highchair,booster seat,babygate,toys,movies,books,games,cooler & fans, Wifi 600mbps. Minimum age 25. LIC STR22-00

FamilyValueAir conditioning

Top guest favourite
A cozy living room features a full sofa, a comfy chair, and a rustic coffee table set on a striped rug. A gas fireplace is set into a stone wall, while large windows offer mountain views. Blinds provide adjustable light control.
Apartment in Winter Park
5 out of 5 average rating, 103 reviews

Cozy DT condo mins from slopes

Welcome to your perfectly located ski getaway! This updated 2BD/2BA Beaver Village condo has its own shuttle line with the bus stop just a few steps from your door, bringing you directly to the Winter Park Ski Resort Village! The shops and restaurants of Cooper Creek and DT Winter Park are a short walk away. The well-equipped kitchen is upgraded with all new appliances, and fiber internet allows for remote work and streaming TV. Finally, warm your bones in the multiple hot tubs and sauna!

FamilyLocationAmenities

Top guest favourite
A serene outdoor space features smooth stones lining the banks of a gentle stream. Two wooden Adirondack chairs are positioned on the grass, offering views of the water. Lush greenery and trees frame the scene, contributing to a peaceful natural setting.
Apartment in Winter Park
4.89 out of 5 average rating, 397 reviews

Riverfront Condo☆1st Floor☆Ski Bus☆Pool & Hot Tub

Recently remodeled 1st floor condo with views and sounds of Fraser River. Walking distance to downtown Winter Park grocery store, coffee shop, restaurants, breweries, retail stores, bars, movie theater, and bowling alley. Community amenities include an indoor pool, hot tubs, workout room, lounge with pool table, laundry facilities, and outdoor playground. Free bus to resort nearby. This riverfront condo is perfect for relaxing and unwinding after a full day of outdoor activities.

ValueFamilyAccuracy

Top guest favourite
The image captures a scenic view of a mountain resort village, featuring multiple buildings and a ski slope in the background. Snow-covered trees line the pathway, while outdoor seating with umbrellas is visible in the foreground, inviting relaxation in the crisp mountain air.
Apartment in Winter Park
4.91 out of 5 average rating, 276 reviews

Ski-In Ski-Out Zephyr Mtn Lodge Condo w/ Hot Tub

Enjoy your stay right next to the Gondola here at the Zephyr Mountain Lodge - Winter Park Resort's premier ski-in/ski-out base lodging. This 1-bedroom, 1-bathroom condo is ideal for a small family or couple seeking mountainside convenience and complimentary amenities. Enjoy a direct ski-in/ski-out location, where winter adventures and summer endeavors are easily in reach! End each day with ease - whether you're soaking in the community hot tub or warming up by the unit’s fireplace.

ValueFamilyBathroom

Top guest favourite
A cozy living space is featured, showcasing a dark leather sofa with a lavender throw pillow. A wall-mounted television is positioned above a white-brick fireplace. Light hardwood flooring extends throughout, while large windows allow natural light to brighten the room.
Townhouse in Winter Park
4.94 out of 5 average rating, 102 reviews

Beautiful Condo at Winter Park!

Beautiful one bedroom condo that sleeps up to 6 and situated at one of the best locations at Iron Horse. All amenities including pool, hot tub, fitness center, and garage are in the same building! Walk across the sky bridge and you’re at the corridor run connecting the base of Mary Jane to the base of Winter Park. Condo includes a king, queen Murphy, and one queen plus bed from a new American leather sleeper sofa. Completely equipped kitchen and great place for all activities!

LocationFamilyBiking

Guest favourite
A spacious living room is highlighted by large floor-to-ceiling windows that frame expansive mountain views. A cozy mid-century sectional sofa is positioned on a light-colored area rug, with natural light enhancing the inviting atmosphere. A glimpse of the kitchen is visible in the background.
Apartment in Winter Park
4.96 out of 5 average rating, 119 reviews

Luxury Ski-In/Out | Ski to Winter Park Resort

Elevate your getaway in this cozy mountain condo, wrapped in mid-century charm and breathtaking views. Enjoy the mini Pub, snuggle up by the fireplace, or take in the mountain views. Sleep in luxurious comfort, and dine with a ski lift mural as your photo-worthy backdrop. Put a vintage record on, host a game night marathon, or soak in the infinity-style hot tub. The slope is located directly behind the building and you can walk or ski to the Winter Park Resort village center.

ValueFamilyKitchen

Guest favourite
The exterior of the condo complex is visible, showcasing multiple levels adorned with windows. Snow blankets the landscape, while a heated outdoor area features seating and a hot tub. Mountain views provide a scenic backdrop, emphasizing the peaceful surroundings.
Apartment in Winter Park
4.88 out of 5 average rating, 217 reviews

One Bdrm Condo Ski In / Ski Out, Hot Tub, Fire Pit

Located in the Winter Park Village, walking distance to The Gondola this condo has it all! The bedroom features a King bed with a memory foam pull out Queen in the living area. Complete Kitchen, full size fridge, dishwasher, large bathroom, and private covered patio with views of the Mountain. Walking distance to shopping, restaurants, & activities! One of only a handful of units with direct outdoor access. UPDATE: New hot tub is OPEN! Permit #009238

FamilyValueHiking

Top guest favourite
Apartment in Winter Park
4.94 out of 5 average rating, 34 reviews

Trestle Bike Park•Hot Tub•Pet Friendly•Mtn View

Cozy mountain studio on the Mary Jane Corridor near Trestle Bike Park and Winter Park Village. Perfect for summer mountain biking, hiking, and outdoor adventures. Features a queen bed, sofa bed, full kitchen, electric fireplace, fast Wi Fi, and spacious bathroom with tub and separate shower. Enjoy the outdoor hot tub, gym, free laundry, grill area, trail access, uncovered parking, and pet-friendly accommodations. The Studio doesn’t have AC unit.

LocationFamilyAmenities

Guest favourite
A tastefully arranged sleeping area features a dark green accent wall and a modern bed with neutral bedding. A stylish nightstand with a small plant and clock is positioned beside the bed, illuminated by a sleek wall-mounted lamp.
Apartment in Winter Park
4.9 out of 5 average rating, 243 reviews

Ski In/Ski Out - Modern Cozy Condo in Winter Park

Leone’s Den | A Boutique Mountain Retreat at the Base of Winter Park Resort Step into refined alpine comfort at Leone’s Den, an elegant studio just steps from the slopes. Located across from the Village Base, enjoy easy access to dining, shopping, and après-ski, then retreat to a warm space with a cozy fireplace and elevated finishes. Relax in Winter Park’s largest hot tub and return to plush linens and beautiful mountain and village views.

LocationValueIndoor spaces

Top guest favourite
The living area features a comfortable sofa and armchair, centered around a coffee table. A round dining table with four chairs sits in view of a kitchen bar with pendant lighting. Natural light enters through large windows, enhancing the cozy atmosphere.
Apartment in Winter Park
4.96 out of 5 average rating, 164 reviews

Top floor, larger 1 bedroom in Winter Park Village

Conveniently located in the Winter Park Village at Fraser Crossing, this updated and oversized 1 bedroom condo sleeps 4 comfortably with a FULL KITCHEN!!! Enjoy the views that come with this peaceful and conveniently located penthouse unit. Close to entertainment, activities, restaurants, ice skating rink, and adventure! Most importantly, a short 2 minute walk to the Gondola...park your car and forget about it.

LocationFamilyCondition

Guest favourite
The living area features a spacious sofa adorned with patterned pillows, and a coffee table sits on a patterned rug. Large windows allow natural light to fill the room, offering views of the surrounding mountains. A fireplace is positioned beneath the mounted television.
Apartment in Winter Park
4.89 out of 5 average rating, 337 reviews

Oversized 1bed Ski In/Out MTN VIEWS King&Qn beds

Oversized 1 bed in Zephyr Lodge, WP's only ski in/out condos. 20% larger than other 1 Beds w/ views of the mtn slopes & village. King bed in Bedroom + queen murphey in living room. Amenities: Window AC unit, ground level ski locker, outdoor hot tubs & fitness center. One Private underground parking for guests (summer free/winter $30 /day). Near starbucks, ski rental, shops, & restaurants!

FamilyLocationAmenities

Top guest favourite
A modern building is visible on the left, surrounded by snow-covered ground and tall evergreen trees. A clear blue sky is overhead, with the sun shining brightly in the upper right corner. A snow-packed path leads through the winter landscape, inviting exploration.
Flat in Winter Park
5 out of 5 average rating, 45 reviews

Modern New build ski in/out. 1br + den.

**Charming New Build in Winter Park - Steps from the Trail!** This cozy retreat features a comfortable living room with a queen sofa bed, an office/den equipped with full-size bunk beds, and a single bedroom with a luxurious king-size bed. Enjoy all the modern comforts, including WiFi, a fully equipped kitchen, a washing machine, and essentials like a coffee maker, toaster oven, and blender.

LocationValueGetting around

Popular amenities for Winter Park ski-in/out rentals

When is the best time to visit Winter Park?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$356 SGD$400 SGD$386 SGD$224 SGD$170 SGD$182 SGD$196 SGD$192 SGD$168 SGD$182 SGD$224 SGD$407 SGD
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