Condo holiday rentals in Winter Park

The welcoming living area showcases a spacious sectional sofa adorned with a colorful throw. A stone accent wall complements the large flat-screen smart TV. Natural light enters through expansive windows, illuminating the area, while a modern counter separates the kitchen from the living space.

4.94 out of 5 average rating, 140 reviews

Cozy mountain retreat in downtown Winter Park

Lovingly remodeled Hi Country Haus 1 bedroom 1 bathroom condo central to downtown Winter Park. Use our Tiny Mountain Retreat as a launchpad to all the local access Winter Park has to offer or as a space for rejuvenation in this beautiful mountain town. Incredible access to local trail running, mountain biking, backpacking, fly-fishing, hiking and skiing. Grand Lake and Rocky Mountain National Park are easily and often visited from our spot as well. WP Short-term rental registration #019404

The fully equipped kitchen features wood cabinetry, modern appliances, and a large island with seating for four. A dining area with a circular table and four chairs is positioned nearby. Warm lighting is provided by a decorative pendant fixture, enhancing the cozy ambiance.

4.93 out of 5 average rating, 264 reviews

Top Floor Condo Steps From Free Shuttle w/Hot Tub

Two bedroom, Two bath, top floor condo with three private balconies. Our fully equipped kitchen comes complete with all the amenities you need to prepare your favorite meals, and we provide complimentary toiletries for your convenience. 15 minute walk to main street bars and restaurants and on the free ski shuttle line to the Mountain or Main Street. Take advantage of our free parking in front of the building and unwind after a long day on the slopes or trails in the community outdoor hot tub.

A modern studio is presented, featuring a well-equipped kitchen with bar stools at the counter. Two armchairs sit on a patterned area rug, and a spacious bed is visible in the foreground. The design incorporates neutral tones and textured wall tiles.

4.88 out of 5 average rating, 233 reviews

Homebase Snowblaze

Enjoy the magic of the Fraser River Valley and charm of downtown Winter Park from our well-equipped, completely remodeled studio. Only an hour and thirty minute drive from Denver International Airport. Walking distance to Winter Park's Main St. lined with shops and dining and a quick 5 minute drive to the world class slopes of Winter Park resort. Take advantage of the free "Lift" bus, with a stop right out front of the building and a ride to the resort in less than 5 minutes. WP STR # 009036.

4.97 out of 5 average rating, 110 reviews

Condo Overlooking River in Town of Winter Park

Our Condo overlooks the beautiful Fraser River close to downtown Winter Park in the heart of the Rocky Mountains. Just a few minute walk to restaurants, pubs, shops, hiking trails, and all that Winter Park has to offer! Soak in one of the hot tubs at the nearby clubhouse after a full ski day or cool off in the indoor pool after adventuring out on a hike or bike ride. Enjoy the convenience of the winter ski shuttle (Blue line) behind the building for a 15-minute ride to Winter Park Ski Resort.

A stone fireplace is centered in the room, flanked by a television mounted on the wall. A dining table with two red dishes sits in front of the fireplace, while a photo of a bear adorns the wall above. Warm tones create a cozy setting.

4.89 out of 5 average rating, 118 reviews

Bear's Den

New! Kick back and relax in this beautifully remodeled, ground level studio. Fully equipped kitchen, stone fireplace, queen size bed and pull out sofa. Large covered patio too with mountain views! Ski Granby Ranch or Winter Park, visit Grand Lake, Hot Sulphur Springs, Rocky Mountain National Park and more! Horseback riding, Sleigh rides, Tubing, Snowmobiling, Boating, Kayaking, Paddle boarding, Fishing, Golf, Swimming. It's all here! Check in is at 4:00 pm and check out is at 10:00 am.

A rustic stone wall forms the backdrop for a warm living area. A wooden shelf displays decor above a modern fireplace. A small Christmas tree decorated with lights is positioned nearby. A wooden table is adorned with a decorative tray holding three candles.

4.92 out of 5 average rating, 190 reviews

Cozy 2BR/2B Condo on Winter Park bus route

Your peaceful, yet adventurous, vacation in the mountains starts here. This cozy condo is on the second floor of the Silvercrest Condominiums. The condo has a fully stocked chef’s kitchen, wifi, cable tv, private balconies off each bedroom and the living room, games, a washer and dryer, and Colorado and outdoor books available for your enjoyment. It is located a short drive from Winter Park and Mary Jane resorts as well as just minutes from the grocery store, restaurants, and breweries.

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.

A scenic mountainous landscape is showcased, with snow-covered peaks under a clear blue sky. The foreground features a line of trees and a snow-blanketed ground, while distant mountains create a dramatic backdrop.

4.94 out of 5 average rating, 102 reviews

Amazing Top Floor WP Getaway!

Beautiful condo with excellent access to all Winter Park has to offer! Relax by the wood burning fireplace after a day of the world's best skiing (the shuttle picks up right out front), hiking, mountain biking. 1/4 mile walking trail (or 3 minute drive) drops you right in the heart of Winter Park. Amazing views from three decks! Includes underground parking, ski locker, hot tubs, pool, exercise room, game room, bar, and restaurant within the building. Fully equipped kitchen.

An aerial view showcases the condominium complex nestled alongside a flowing river, surrounded by lush greenery. The nearby trees enhance the natural setting, while the buildings feature a contemporary design with flat roofs and balconies overlooking the scenic landscape.

4.81 out of 5 average rating, 318 reviews

Michael’s Dream Condo #16, Winter Park

Located in Downtown WP, Condo 16, 3rd floor, awesome views, High Country Haus Condominiums. Lic#005206. Check out WP resort for exciting new activities. World class skiing, cross country, snowmobile, bike, hike, fish, restaurants, shops, Hideway Park (sledding hill, WALK TO Fireside Grocery Market, Great WiFi, Grand Park Rec Center. HCH Condos Rec center has pool/jacuzzi’s, billiards, gym. WP RESORTS FREE BUS pick up is across our parking lot.

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, 205 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.

A studio layout is presented, featuring a spacious bed with neutral bedding. A bunk bed is positioned nearby, and a set of skis is mounted on the wall. Two windows allow natural light to fill the space, complemented by a comfortable seating area with armchairs.

4.89 out of 5 average rating, 141 reviews

Studio Condo in the Heart of Winter Park! lic#9602

You're steps from terrific shops, bars, and restaurants. Right outside the condo is the free bus stop to world-class skiing at Winter Park. It is a 3-minute bus ride and frequents every 15 minutes in the winter. Free covered parking is included on a first-come basis. All new kitchen appliances installed in February 2024! Note: There's no A/C in the unit, but there is an evaporative cooler to help keep the unit cool in summer.

Two teal chairs are positioned on a balcony, facing a snow-covered landscape. The sun shines brightly in the clear sky, illuminating distant mountains and a frozen river below, creating a serene outdoor setting.

4.97 out of 5 average rating, 118 reviews

Walk to Restaurants! Private Patio!

Book now for winter weekends! Don’t miss this spacious 1 BR Fraser condo perfectly located for your winter adventures in Grand County. You are just a short walk from the grocery store, restaurants, breweries and the Fraser River and Trail. You are a .8 mile walk from the train station which offers daily Amtrak service and weekend Ski train service in the winter. You are also steps away from the free Lift shuttle service.

Popular amenities for Winter Park condo rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Weekly condo rentals

5 out of 5 average rating, 79 reviews

NEW+ Ski Winter Park+ Hot Tub+ Garage+ Boot Dryer

4.94 out of 5 average rating, 50 reviews

Steps to Dining | Free Shuttle | Hot Tub

A cozy living room features a modern gas fireplace below a wall-mounted TV. Large windows allow natural light to brighten the space, showcasing a view of the surrounding mountains. Two blue accent chairs sit opposite a gray sofa, with a patterned area rug adding warmth.

4.89 out of 5 average rating, 98 reviews

Luxury Winter Park condo with mountain views

A spacious King bed is dressed in a textured white coverlet, complemented by a soft grey decorative pillow with the word 'Happy.' A large landscape photograph featuring snowy trees and a blue sky hangs above the headboard, adding a touch of nature to the room.

4.91 out of 5 average rating, 82 reviews

Stylish Studio on Main Street in Winter Park

A cluster of condos is nestled in a snowy landscape, showcasing multiple balconies with wooden railings. The building's exterior is highlighted by its muted tones against a clear blue sky, while snow blankets the ground and clings to the edges of the structure.

5 out of 5 average rating, 32 reviews

Mountain Adventure Condo in Fraser!

A spacious living area features large windows that allow natural light to fill the space, showcasing scenic views of the surrounding landscape. Comfortable seating is provided with a leather sofa and a cozy chair, complemented by a decorative area rug and a stylish dining table nearby.

5 out of 5 average rating, 23 reviews

Modern Luxury: WP Town Walkable, Hot Tub, W/D, a/c

An aerial view captures a modern two-story condo building, highlighting its contemporary architecture. Surrounding mountains are visible in the background under a clear blue sky. The landscape features a mix of gravel and grass, enhancing the serene setting of the property.

4.95 out of 5 average rating, 60 reviews

NEW Condo -Ski/Bike/Hike Winter Park/Grand County

Superhost

A cozy sleeping area features a quilted bedspread adorned with bears and trees, complemented by decorative pillows. Framed artworks hang on the wall above the bed. Light-colored walls and natural stone flooring enhance the warm ambiance, while a kitchenette area and seating are within view.

4.73 out of 5 average rating, 97 reviews

River View Studio Near Winter Park Ski Resort

Pet-friendly condo rentals

A warm living area features a wood-burning fireplace framed by wooden paneling. A cozy rug is positioned in front, with a dog resting beside it. Above the fireplace, a framed artwork adds a decorative touch, while additional items are arranged on the mantle.

4.93 out of 5 average rating, 103 reviews

Cozy Mountain Getaway - Minutes to Winter Park

An open-concept living area presents a stone fireplace and vaulted wooden ceiling. A dining table with black chairs is positioned beside a fully equipped kitchen featuring stainless appliances and granite countertops. Natural light filters in through large windows, highlighting the cozy seating area.

4.94 out of 5 average rating, 157 reviews

Hideaway Park! Hot tub,Pool,FitnessCtr&FreePrkg

A serene snowy landscape showcases dense evergreen trees blanketed in fresh snow. The balcony railing is visible, providing a view of the winter scene. Soft light filters through the branches, creating a peaceful atmosphere in the surrounding nature.

4.74 out of 5 average rating, 191 reviews

Great Condo right on the Creek License #005702

A spacious living area features a red seating arrangement with a comfortable sofa and armchair, complemented by light streaming through multiple windows. A kitchen island with a sink is visible, alongside a dining area that includes four chairs. A stone fireplace adds a touch of warmth to the space.

4.85 out of 5 average rating, 465 reviews

Cozy 1 bedroom Granby Ranch condo

4.91 out of 5 average rating, 138 reviews

Tall Timbers of the Rockies

A comfortable living area features a large television mounted on the wall above a wooden entertainment unit. The unit contains books and decorative items. A clear view of the kitchen and dining area is visible in the background, along with modern appliances and a casual seating arrangement.

4.99 out of 5 average rating, 118 reviews

Winter Park Getaway for Mountain Biking/Hiking!

A dining area showcases a table set for four, complemented by green placemats and glassware. A flat-screen TV is mounted on a wood-paneled wall, while a stone fireplace adds warmth to the space. A nature-themed artwork enhances the atmosphere.

4.88 out of 5 average rating, 552 reviews

Granby Mountain Retreat

A modern kitchen area features wood cabinetry and stainless steel appliances, including a refrigerator and microwave. A dining table with two chairs is positioned nearby, complemented by a cozy gray armchair. The space is illuminated by ceiling lights, enhancing the inviting atmosphere.

4.83 out of 5 average rating, 520 reviews

Luxurious Mountain Condo

Condo rentals with a pool

A cozy living area features a stone fireplace with a wooden mantle. A flat-screen TV is positioned on an oak cabinet. Light filters through sheer curtains, illuminating a comfortable green armchair and a patterned sofa, accompanied by a wooden coffee table at the center.

4.86 out of 5 average rating, 117 reviews

Beaver Village in Winter Park - 2br/2bath Condo

Superhost

The living area features a comfortable seating arrangement with wooden chairs and a coffee table. A television is mounted above a fireplace, while a clock and books are displayed on a shelf. Large sliding glass doors provide access to outdoor views.

4.8 out of 5 average rating, 215 reviews

Great View, pool & hot tub, 1 bed & loft sleeps 6

Superhost

The exterior of the building showcases a four-story structure with a mix of red and stone finishes. Lush greenery surrounds a stone fire pit and seating area, while mountains are visible in the background under a partly cloudy sky.

4.82 out of 5 average rating, 146 reviews

Winter Park 2bd/2ba (Sleeps 6) - Ideal Location!

A cozy seating area features a dark sofa adorned with soft pillows, positioned beside large windows with yellow curtains. A wooden coffee table is set with a plate of fruit and a book, while a warm light fixture hangs overhead, enhancing the inviting ambiance.

4.87 out of 5 average rating, 405 reviews

Cozy Studio~Mtn Views~Salt Water Pool & Hot-Tubs

A cozy living room features a comfortable armchair with an ottoman, a wooden TV stand with decorative elements, and a fireplace set against a textured wood wall. Natural light filters through sheer curtains, highlighting a vintage artwork depicting Winter Park.

4.9 out of 5 average rating, 143 reviews

Cozy 2 bed/2 bath with Hot Tub and Mountain View

4.93 out of 5 average rating, 239 reviews

Pine in the Sky Condo, Cozy + Close to GR/WP/RMNP

A spacious bedroom is furnished with a wooden king bed, layered with a white comforter and a brown throw. Two bedside tables with lamps flank the bed. A colorful autumn-themed artwork adorns the wall above, complementing the warm tones of the decor.

4.95 out of 5 average rating, 124 reviews

Mountain Delight Near Winter Park

A modern living area features a deep blue sofa adorned with decorative pillows, a glass coffee table, and a cozy textured rug. Natural light filters in through large windows, highlighting a dining area and a spiral staircase that leads to the loft space above.