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

An inviting living area features a mix of seating options, including a spacious couch and a rocking chair. A coffee table centers the space, while a kitchen bar with stools offers additional seating. Decorative artwork and a guitar adorn the walls, contributing to a cozy ambiance.

4.82 out of 5 average rating, 112 reviews

Cozy Condo on the Fraser River

Bright airy western sunset view with no obstructions looking down on Fraser river 25' in front of building. Walking distance to all of Winter Park. One year old new Rec Center with pool, hot tubs, pool table, Computer, guitar, great locker rooms with showers. Free town bus comes by hourly and pick up is right at our building. Car not really needed once your here. Winter Park is great Skiing with all the summertime activities as well. Sorry we are not pet friendly. We just installed a new stove.

4.94 out of 5 average rating, 101 reviews

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

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

4.99 out of 5 average rating, 183 reviews

The exterior of the corner unit loft showcases a welcoming entrance with wooden steps leading to a covered porch. Lush greenery surrounds the building, complemented by slender aspen trees and meticulously maintained landscaping that enhances the natural setting.

Loft in Granby

Beautiful Spacious 2 BR & Loft Mountain Condo

Welcome to your perfect mountain escape! From breathtaking views through the large windows & private deck, to easy access to the slopes. Our condo has so much to offer. Located right in the middle of all things Rocky Mountains. You're just 30 minutes from Grand Lake/Rocky Mountain National Park/Winter Park and 2 mins from skiing, fishing, golf, and mountain biking at Granby Ranch. This corner unit is very spacious. The condo is able to sleep 6. We only allow 4 guests-with special exceptions.

4.98 out of 5 average rating, 118 reviews

A warm living area is depicted, featuring a comfortable brown sofa and a matching armchair. A coffee table sits in front of a stone fireplace, which is accompanied by a TV mounted above. Large windows invite natural light and showcase outdoor scenery.

Condo in Granby

Granby Ranch Ski-In/Out – Hot Tub & Firepit

Freshly remodeled in July 2025, Sundog Condo is your cozy ski-in/ski-out retreat at Granby Ranch – just 20 mins to Rocky Mountain National Park, Grand Lake & Winter Park. Enjoy a king bed with Brooklinen linens, fully stocked kitchen (Nespresso, quality cookware), gas fireplace, Roku TV, and patio with firepit. Year-round hot tub steps away; pool & gym access available. Walk to ski lifts; trails, golf, fishing, biking, hiking & skiing/Nordic trails right outside your door - adventure awaits!

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.

4.9 out of 5 average rating, 198 reviews

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

Welcome to Leone’s Den. This newly renovated studio condo located at the base of Winter Park Resort. Walk less than 150 yards to the slopes! Shops, restaurants, and bars at the Village Base just across the street and a pool sized hot tub! Marvel at the beautiful mountain views from the largest hot tub in Winter Park, brand new in 2025. Enjoy the view of village and mountain landscape while enjoying the warmth of the fireplace. The studio has everything you need for an unforgettable stay.

4.92 out of 5 average rating, 178 reviews

A cozy sleeping area features a large bed with a neutral quilt, framed by a wooden sliding door. Symmetrical bedside lights illuminate the space, and a deer antler design is displayed above the headboard, enhancing the rustic mountain aesthetic.

Condo in Granby

The Mountainside at Granby Ranch

This is truly mountainside living with trail & ski access right out the door! We remodeled over 4 months & added a 14 ft live edge bar, 100 year old hardwood vanities and many other touches to make the mountainside a memorable Colorado experience. While staying you can enjoy all that Granby Ranch has to offer in every season or access Winter Park or Grand Lake in quick 20 minute drives. A grocery store and gas station are only 5 minutes away and Granby is right around the corner. Enjoy!

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.

4.89 out of 5 average rating, 385 reviews

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

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. It is a great place to curl up next to the electric fireplace, relax, and unwind after a full day of outdoor activities.

4.99 out of 5 average rating, 141 reviews

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

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.

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.

4.97 out of 5 average rating, 109 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.

A cozy living area features a brown sofa adorned with decorative pillows and a striped armchair near a window. A dining space with wooden chairs and a table is visible, while a snowy outdoor view includes a bridge decorated with a festive wreath.

4.96 out of 5 average rating, 137 reviews

Amazing Condo at the Base of Winter Park Resort

Our home at the base of the Winter Park Resort (100 meters from the Gondola) is updated (paint, furniture, lighting, bedding, kitchen supplies), clean, and modern to provide a cozy and comfortable base for every mountain activity: Ski, bike, play, hike, relax, and renew with a hot tub only 2 meters away. King bed, comfortable queen sleeper and a port-a-crib if you need it make this great for a family/group retreat. Winter Park Short-Term Rental Registration No. 4328

Superhost

A sign indicating the various snow depth measurements at Winter Park is partially buried in snow, with visible markers at six-inch intervals up to 18 inches. The forest backdrop is lined with snow-covered trees, creating a peaceful winter scene.

4.78 out of 5 average rating, 273 reviews

Michael’s Dream Views in Winter Park, CO condo #15

Located in Downtown WP, Condo 15, top floor, awesome views, in Hi Country Haus Condominiums, Lic#009357. Check out WP resort website for exciting improvements. World class skiing, biking, hike, fish, restaurants, shops, breweries, Hideway Park (sledding hill, Concerts, skateboard). WALK TO Fireside Grocery Market, Foundry Movies/Bowling/Pizza, Grand Park Rec Center and more. HCH has exclusive Rec center. WP RESORTS FREE BUS, pick up across our parking lot.

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.

4.87 out of 5 average rating, 195 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

Popular amenities for Winter Park ski-in/ski-out rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Ski-in/ski-out house rentals

5 out of 5 average rating, 18 reviews

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

Devil's Thumb - Modern Mountain Retreat

5 out of 5 average rating, 22 reviews

A modern kitchen and dining area features a large central island with seating for four. Light wood cabinetry complements the neutral decor. Floor-to-ceiling windows provide expansive views of the outdoors, while a stone accent wall adds a touch of warmth to the space.

Home in Granby

Modern Mountain Retreat w/ EV

5 out of 5 average rating, 5 reviews

Home in Granby

Private Hot Tub! Stunning Luxury Home, Ski-In/Out

5 out of 5 average rating, 38 reviews

A modern custom home features a mix of stone and wood exteriors, framed by a gently sloping driveway. The design highlights large windows and slanted roofs, with solar panels visible on the roof. Surrounding natural landscaping adds to the mountain setting.

Home in Granby

Colorado's Coolest Ski In/Out Home

Superhost

A warm kitchen area features granite countertops with a sink and seating for two at the breakfast bar. The adjacent dining space includes a wooden table set for six, surrounded by natural light filtering through nearby windows, complemented by rustic decor on the walls.

Home in Winter Park

4.85 out of 5 average rating, 60 reviews

Beautiful Ski-In Home, with Hot Tub!

4.93 out of 5 average rating, 70 reviews

A spacious living area features a stone fireplace as the focal point, flanked by comfortable seating arranged on a warm carpet. A flat-screen television is mounted on the wall, and large windows allow natural light to fill the room, complemented by wooden beams on the ceiling.

Home in Winter Park

Mountain Escape Minutes From WP | Hot Tub Access

4.98 out of 5 average rating, 87 reviews

A spacious three-level lodge is nestled in a snowy landscape, featuring a blend of stone and stucco exterior. Snow-covered pine trees surround the home, and large windows offer glimpses of mountain views in the distance.

Home in Fraser

Winter Park Free Ski Shuttle+MountainViews+Hot Tub

4.94 out of 5 average rating, 229 reviews

The exterior of the house is presented against a bright blue sky, surrounded by tall pine trees. A spacious deck extends along the upper level, while a snow-covered landscape enhances the setting. The structure comprises multiple levels, showcasing a blend of natural materials.

Home in Tabernash

Million Dollar Views

Family-friendly, ski-in/ski-out home rentals

The living room features a light-coloured leather sofa and loveseat, positioned around a central coffee table. A modern television is mounted near a cozy gas fireplace, and ample natural light enters through partially drawn blinds. Decorative accents include art on the walls and small potted plants.

4.85 out of 5 average rating, 89 reviews

5th-Fl With Views! Full Kitchen! Luxe Sleeper Sofa

The studio features a fully equipped kitchen with granite countertops and modern stainless steel appliances. A seating area is arranged with a small dining table and chairs next to large windows, allowing natural light and a view of the outdoor landscape.

4.97 out of 5 average rating, 59 reviews

Remodeled Ski In/Out Condo. 30 Sec Walk To Slope!

A cozy living area features a green sofa and a striped armchair. A wooden dining table and chairs are positioned nearby, with pendant lighting above. The kitchen showcases stainless steel appliances and warm cabinetry, enhancing the inviting space.

4.9 out of 5 average rating, 299 reviews

One Bedroom Condo - Winter Park Resort Base Area

Superhost

5 out of 5 average rating, 3 reviews

Condo in Winter Park Ski and Mountain Views

An aerial view captures a snowy landscape surrounding a vibrant lodge complex. The buildings exhibit a mixture of colors and architectural styles, nestled amidst evergreen trees and ski slopes. A circular drive is visible at the forefront, with vehicles parked along the entrance.

4.94 out of 5 average rating, 51 reviews

Zephyr Mountain Lodge - 1BR Beautifully Renovated

A modern condo building stands against a clear blue sky, showcasing a contemporary design with a mix of dark and light materials. Large windows enhance the building's exterior, while a stone base provides stability. Surrounding snow-covered ground and evergreen trees complete the winter setting.

5 out of 5 average rating, 7 reviews

Ski In/Ski Out 2bdrm Winter Park

An airy studio condominium features a curtain-draped sleeping area with a queen-sized bed, adorned in a patterned quilt. In the living area, a gray sofa and a wooden coffee table are positioned near a dining space, which includes four chairs and a view into a kitchen.

4.92 out of 5 average rating, 85 reviews

Large studio condo downtown Winter Park, CO

A spacious living area features leather sofas arranged around an inviting fireplace. Two ottomans and a large television are positioned nearby, while natural light streams in through large windows adorned with wooden frames.

4.93 out of 5 average rating, 55 reviews

10 Minute Walk to the Winter Park Gondola 6 beds.

Ski-in/ski-out cabin rentals

5 out of 5 average rating, 11 reviews

A two-story ski cabin is seen surrounded by snow-covered landscapes, featuring a warm wooden exterior. A set of stairs leads to a deck above, where seating arrangements are visible. Tall trees and mountains in the background provide a serene, natural setting.

Cabin in Dillon

Chic Ski Cabin, 1Mi to Gondola

5 out of 5 average rating, 49 reviews

A spacious cabin is nestled among towering pine trees, showcasing a blend of wood and stone in its exterior. Snow blankets the surrounding ground, while sunlight filters through the trees, highlighting the cabin's architectural features and inviting porch.

Cabin in Fraser

Moose Pads Near Winter Park-30 Day Minimum!

4.99 out of 5 average rating, 90 reviews

Cabin in Black Hawk

Cozy Forest Lodge-Hot Tub, Game Room, Trails, Pets

The custom log home is nestled in a snowy landscape, featuring large windows that invite natural light. A stone foundation supports the structure, while a two-car log garage stands nearby. Pine trees outline the property, providing a serene and rustic setting.

Cabin in Breckenridge

Custom Ski-in/Ski-Out Log Home in Breckenridge

4.71 out of 5 average rating, 14 reviews

A log cabin with a wooden deck is surrounded by snow-covered ground. Two life-size deer sculptures are positioned in the foreground, while trees and a clear blue sky are visible in the background. The cabin features large windows and natural wood finishes.

Cabin in Breckenridge

Breckenridge Cabin

A mountain house is positioned amidst autumn foliage, with a driveway leading to the garage. Chairlifts are visible in the background, framed by a panoramic sky filled with clouds. Surrounding trees and golden grasses complete the natural setting.

Cabin in Granby

4.92 out of 5 average rating, 13 reviews

Ski in Ski out House with stunning mountain views!

5 out of 5 average rating, 28 reviews

A cozy bedding arrangement features a rustic wooden headboard and various decorative pillows with bear motifs. A soft, textured throw blanket drapes over the edge of the bed, while a nightstand holds a stylish lamp and a small potted plant, contributing to the calming atmosphere.

Cabin in Black Hawk

Couples Private Getaway- Hot Tub /Views / Ski