11 Best Luxury Rentals in Winter Park Colorado

Winter Park, Colorado, is a top destination for winter sports enthusiasts. While we’re not expert skiers, we love spending time here for the luxurious mountain getaway experience. From world-class skiing and snowboarding on pristine slopes to cozy evenings by the fire, this charming town always gives us new reasons to return. If you’re planning an extended stay, consider booking one of the best rentals in Winter Park Colorado. To save you time, we’ve handpicked our favorites! These rentals offer the perfect base for exploring the vibrant winter wonderland, whether you’re an avid skier or simply looking for a peaceful retreat.

Lakota Vista

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Kicking off this list is Lakota Vista, a rental directly across from Winter Park Resort in the Lakota neighborhood. As a group, we had ample space to spread out in this five-bedroom custom mountain home. The high-end amenities throughout the house elevated our experience, and the sweeping vistas from the deck, patio, and private hot tub were simply breathtaking. We spent many evenings soaking in the views and enjoying the peaceful mountain atmosphere.

What was our favorite spot? The main living area! We loved warming up by the gas fire while watching the game on the large flat-screen TV, all while enjoying stunning views of Winter Park Resort through the huge windows. The kitchen, complete with stainless steel appliances, also made meal preparation a breeze, and the eight-person dining table was ideal for both celebratory dinners and casual takeout meals.

The sleeping arrangements were also ideal for our group. The primary king suite on the main level was luxurious, and the two additional king suites on the lower level, each with its own ensuite bathroom, provided ample privacy and comfort. Lastly, the bunk rooms on the lower level were designed for kids.

Trademark Views

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Trademark Views is easily one of the top rentals in Winter Park CO. Being just a half-mile from the slopes was incredibly convenient, and the amenities provided were perfect for a relaxing ski vacation. We especially appreciated having a private washer/dryer, high-speed Wi-Fi, and of course, the blissful private hot tub. The fact that cribs and air mattresses were available upon request was also a huge plus for our family.

Inside, the spaciousness and the breathtaking views (hence, the name) truly impressed us. The soaring ceilings and walls of windows were nothing short of grandeur, and the floor-to-ceiling rock fireplace in the living area became our favorite gathering spot. The plush leather furnishings were incredibly comfortable, making it easy to relax and enjoy the majestic mountain panoramas. Additionally, we also loved the convenience of being able to control various aspects of the house, like the temperature and garage door, through the intuitive web app.

The top-floor primary suite was a true highlight of our stay. The vaulted ceilings and spa-inspired bathroom felt incredibly luxurious. Nothing could beat the feeling of soaking in the jacuzzi tub and wrapping ourselves in the robes.

Timber Top Luxury Home

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Perched on a hill overlooking Winter Park, the location of Timber Top Luxury Home couldn’t have been better. We were just a short drive from the Winter Park Resort, easily accessible by the free shuttle. Additionally, the views were simply breathtaking, with panoramic vistas of the Continental Divide and the valley below. Every window offered a postcard-worthy scene, and the designer furnishings throughout the home were to die for.

We especially loved the outdoor spaces at Timber Top. The large rear patio was instantly our favorite spot for wildlife viewing, and the professional Weber grill was perfect for our evening cookouts. Moreover, we also enjoyed hiking and exploring the nearby trails.

Inside, the home was equally impressive. The vaulted ceilings and high-end finishes created a sense of grandeur, and the chef’s kitchen, complete with granite countertops and stainless steel appliances, was a dream to cook in. Meanwhile, the radiant in-floor heating was something that we didn’t know we needed before. The added amenities, like the smart TVs, board games, and even locally roasted coffee, made our stay even more enjoyable.

Zephyr Mountain Lodge 2703

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Best for Smaller Groups. The Zephyr Mountain Lodge 2703 was a fantastic home for us, but we were extremely shocked by the sheer size of this penthouse. The vaulted ceilings and the massive, 17 ft picture windows truly made the space feel expansive and airy. The views were simply breathtaking, and we had unobstructed panoramas of the slopes, the new 10-person Gondola, as well as the charming Winter Park Village below.

Beyond the stunning views and stylish interior, the functionality of the condo really impressed us. With two-bedroom suites, three full bathrooms, and a bunk room perfect for kids, there was ample space for our group. Moreover, the sleeping arrangements were ideal, comfortably accommodating up to 10 people.

The lodge itself offered a wealth of amenities that enhanced our stay. We made good use of the multiple hot tubs after skiing, and the underground parking was a huge plus for us. The workout facility was also a nice perk. Furthermore, being nestled amongst restaurants, shops, and family-friendly activities in Winter Park Village meant we never had to venture far for dining or entertainment.

Mary Jane’s Dream Home

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Now, let’s talk about Mary Jane’s Dream Home, one of the most beautiful holiday rentals in Winter Park Colorado. Nestled in Bridger’s Cache with ski-in/ski-out access, the location was perfect. The home beautifully combined mountain charm with modern style. Huge windows and balconies showcased the stunning winter scenery. We instantly felt relaxed and knew this was a special retreat.

Inside, the luxurious atmosphere was exactly what we expected. The open living room with a grand fireplace was perfect for gathering. We also loved the gourmet kitchen, which made cooking a breeze. We enjoyed dining at the large table or outdoors on the patio. During our stay, we also loved relaxing in the hot tub under the stars. But if that’s not your cup of tea, head to the lower level and check out the wet bar and foosball table.

The four spacious bedrooms, including the king suite and bunk room, comfortably slept everyone in our group. Additionally, the heated garage, boot dryers, ski storage, and heated floors were all very convenient. From the kitchen to the cozy living spaces and easy ski access, Mary Jane’s Dream Home exceeded our expectations.

Base Camp 490

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Best Amenities. The Base Camp 490 is a luxury mountainside chalet with a sprawling 3,800 sq ft floorplan. Once we were inside, we were in awe. The open living space was ideal for relaxing after a day on the slopes, as well as for cozying up for some evening board games with family and friends. Also, the kitchen! As foodies, we were in heaven. It’s truly a gourmet chef’s dream, complete with a Wolf range, Sub-Zero refrigerator, and stunning granite countertops. We cooked several delicious meals after skiing and biking at Winter Park Resort.

The layout of the townhome is fantastic. The first level, with the garage, entryway, fourth bedroom, full bathroom, and bonus sleeping area, offered great privacy. Moreover, the second level was the heart of the home, with the open-plan living space, kitchen, and dining room flowing seamlessly together. The decks on both the front and back were a huge plus, especially with the double-sided gas fireplace that connected the indoor living area to the outdoor deck.

Upstairs on the third level, we found three bedrooms and three bathrooms. The primary suite was particularly luxurious, with a see-through gas fireplace between the soaking tub and the bedroom – talk about romantic! Speaking of relaxation, the private six-person hot tub on the back deck was a lifesaver after a day on the slopes. Soaking our tired muscles while enjoying the mountain views was the perfect way to end the day.

Canopy House

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Nestled amongst the trees in the Bridger’s Cache neighborhood, the Canopy House offered us unparalleled mountain living. The ski-in/ski-out location was a huge plus for us, making hitting the slopes incredibly convenient. But the inside of this house was equally impressive. The dramatic floor-to-ceiling windows and sealed concrete floors perfectly framed the panoramic forest views. We especially loved enjoying our morning coffee on the main level deck, with its outdoor heaters, natural gas grill, and comfortable seating.

After a day on the mountain, the living room was our favorite place to relax. The oversized sectional sofa and cozy gas fireplace were everything. We also loved cooking in the sleek kitchen, which was equipped with high-end appliances like a Sub-Zero refrigerator, Miele dishwasher, Wolf microwave, and Fisher & Paykel range. But if you don’t cook, you can check out the upper-level library instead or relax on the outdoor spa deck with its in-ground hot tub.

Each of the four bedrooms offered us a tranquil retreat with hotel-style luxury linens and private ensuite bathrooms. The Primary King Suite was particularly amazing, with its built-in fireplace, panoramic windows, and private balcony. The Second King Suite was equally stylish and inviting, while the Bunk Suite was great for the kids. Finally, the lower level Queen Suite provided a quiet and comfortable space for other members of our group.

Winterfell at Winter Park Resort

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The Winterfell at Winter Park Resort truly lived up to its hype as one of the best rentals in Winter Park CO, as we felt like royalty throughout our stay. Perched overlooking the slopes of Winter Park Resort and practically nestled in the Arapahoe National Forest, the location couldn’t have been better. From the moment we walked in, we were blown away. The modern architecture and high-end furnishings gave the whole place a luxurious yet comfortable feel. With over 3200 square feet spread across three levels, there was more than enough room for our group.

The main level was the heart of the home, with floor-to-ceiling windows offering breathtaking views of the resort. We spent so much time just gazing out at the slopes – it was mesmerizing. Moreover, the gourmet chef’s kitchen was a dream. With premium Jenn-Aire appliances and every imaginable cooking utensil, we easily whipped up some amazing meals.

The middle level was our favorite for relaxation. The two primary king bedrooms with en-suite bathrooms were nothing short of luxurious. We also loved hanging out on the private deck with a seven-person hot tub. It was the ultimate après-ski treat. The lower level had two more queen bedrooms, a large bathroom, another workspace, and a family room with a huge sofa sectional and a 77” LG OLED TV. This was perfect for our movie nights.

House Rental in Downtown Winter Park on Bus Route

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Best Location. If you want to stay in the heart of Winter Park, this is the place to be. Set in downtown and on a bus route, this Downtown Winter Park House Rental is great for families. The first floor was a hit with our kids. The recreational area was a fantastic space for everyone to hang out. We loved listening to the crackling fire while playing foosball and watching movies. The pool table in the spacious three-car garage was another great addition. We were also surprised when we found a brand new 10-person hot tub.

In addition to the two bedrooms downstairs, a short walk upstairs brought us to two more bedrooms, each with its own bathroom. One room had two queen beds, while the other boasted a new king bed. The main living space on the next floor, though, was the heart of the house. It came with a fireplace that created a warm and inviting atmosphere, and there was plenty of comfortable seating for everyone.

While the house was big and had everything we wanted, the place that we loved the most was the master suite on the top floor. It had a pot belly stove, a cozy seating area, and a separate dressing area. And the bathroom? It was divine! We spent countless hours in the soaking tub.

“This rental treated us like royalty with its entertainment areas, luxurious master suite, and perfect downtown location.”

WOW Travel

Casa de Montana

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Best for Skiing. Everything about Casa de Montana is extraordinary. The mudroom was a godsend for all our ski gear, keeping everything organized and out of the way. Stepping into the main level, we were immediately struck by the gourmet kitchen. The Wolf appliances were a dream to cook with, and the heated deck off the kitchen became our favorite spot for après-ski cocktails under the stars. After dinner, we’d gather in the living room, warming ourselves by the gas fire and reliving the day’s adventures.

The main level king suite was a luxurious retreat, with its own heated deck access, fireplace, and a truly stunning ensuite bathroom. The mid-level, accessible by both elevator and stairs, housed four more king suites, each a private haven with plush linens, beautiful views, ensuite bathrooms, and all the modern amenities we could ask for. We especially enjoyed the wrap-around deck on this level, complete with heaters and a fire pit.

The lower level was the entertainment hub of the house. There, we found a massive media/game room. We spent countless hours playing pool, Mrs. Pac-Man, and just enjoying the space. Beyond that, we also loved to take a dip in the private hot tub while watching other skiers go by.

Ski In Out Luxury Chalet 275

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Best Overall. We had an absolutely incredible stay at Ski In Out Luxury Chalet 275! This stunning 4-bedroom home exceeded all of our expectations. With 4,500 sq ft of luxurious living space, there was plenty of room for our group to spread out and relax. The chalet itself is a masterpiece, boasting breathtaking views of the Continental Divide and nestled in a secluded forest. The ski-in/ski-out access was a major highlight. We loved being able to easily access the slopes of both Mary Jane and Winter Park Resort.

Apart from that, the chalet’s amenities were top-notch, from the gourmet kitchen with appliances to the cozy fireplace in the main living area and the spacious deck. We especially enjoyed the comfortable furnishings, the home theater room, and the radiant in-floor heat, which kept us warm and cozy during the chilly Colorado winter.

We appreciated the thoughtful touches throughout the chalet as well, such as the high-quality bedding, the complimentary coffee, and the well-stocked kitchen. The keyless entry and 24/7 check-in made our arrival and departure a breeze. Everything was truly exceptional.

Our Verdict!

Selecting the ideal holiday rental can be more difficult than you might think. To help you out, we’ve organized the best rentals in Winter Park Colorado above into categories based on the following criteria:

• Best Overall: Ski In Out Luxury Chalet 239
• Best for Skiing: Casa de Montana
• Best Location: House Rental in Downtown Winter Park on Bus Route
• Best Amenities: Base Camp 490
• Best for Smaller Groups: Zephyr Mountain Lodge 2703

Things You May Need During Your Stay

• Warm, winter clothing: Winter Park is located in the Rocky Mountains and experiences cold temperatures and snowfall throughout the winter. So, be sure to pack warm clothing like these winter jackets, snow gloves, and others.
• Camera: Winter Park is a beautiful place with stunning scenery. That said, you’ll want to bring a camera to capture your memories. Check out these Best Buy instant print cameras!
• Snow boots: If you plan on spending time outdoors, you’ll need proper boots to keep your feet warm and dry like these best winter boots.