Holiday rentals with outdoor seating in Winter Park

4.82 out of 5 average rating, 314 reviews

The log cabin is framed by blooming yellow flowers and lush greenery, with a soft sunset sky in the background. Warm light spills from the windows, creating an inviting ambiance that highlights the cabin's rustic charm and natural surroundings.

Cabin in Winter Park

Charming Log Cabin w/hot tub in Winter Park CO!

Authentic Colorado log cabin built in 1972; our 2 bedroom cabin sleeps up to 8 people comfortably. Private deck, luxurious hot tub, ping pong table, gas fireplace, WiFi, games, books & tons of charm. The master bedroom has a queen bed & guest room includes full bed plus bunk bed, air mattress available as well. The ski shuttle stops RIGHT in front of the house. Just a 5 minute walk to park/playground and 10 minute walk to downtown Winter Park. Plush, cozy, a perfect getaway. Town license #5112.

4.98 out of 5 average rating, 190 reviews

An open living area showcases a black leather sectional couch arranged around a circular wooden coffee table adorned with greenery. Wooden accents highlight the walls, while soft lighting illuminates the adjacent kitchen and dining space visible in the background.

Townhouse in Winter Park

Modern/Rustic 2-bedroom Townhouse + Bonus Loft

Newly renovated modern/rustic three-story A-Frame townhome on the free shuttle route. Small and cozy, this 2 bedroom (+ lofted bed) can comfortably accommodate 5, but it should be noted that there's only 1 full bathroom! The location is perfect: it's quiet and serene while only being minutes from downtown Winter Park and two miles from the WP Resort. Vasquez Road is .4 miles from the front door to access everything the National Forest has to offer (hiking, snowshoe excursions, mountain biking)

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.

4.92 out of 5 average rating, 167 reviews

Hideaway Park! Hot tub,Pool,FitnessCtr&FreePrkg

BEST Location in Winter Park!!Trailhead condos offer a year-round heated pool, hot tub, fire pit, patio, clubhouse, large indoor lounge, fitness room & game room. Just steps to Fraser River trail, restaurants, shopping and free ski shuttle. *On Hideaway Park* Access to Summer concerts&festivals, playground, picnic area, fire pit, and skate park to entertain kids! Relax by the fire or private furnished covered deck. Top floor (w/elevator) corner unit w/views! Pets welcome! (w/add'l clean fee).

4.95 out of 5 average rating, 151 reviews

A modern kitchen space is highlighted by a central island with seating for four. Sleek cabinetry in soft colors complements stainless steel appliances, including a refrigerator and a range hood. Pendant lights provide illumination above the island, enhancing the inviting atmosphere.

Flat in Winter Park

Tipsy Fox @ Downtown Winter Park Near the Slopes!

Welcome to the perfect Winter Park getaway! Located in downtown, this cozy one-bed, one-bath condo is just steps away from Hideaway Park and its year-round free events. With 3 queen beds, including a sleeper sofa and a Murphy bed, it comfortably sleeps 6 guests. Enjoy the heated garage and ski locker for your vehicle and snow gear. After outdoor activities, unwind in the hot tub, gather around the fire-pit, or relax on the balcony. Conveniently close to food, slopes, tubing hill, and amenities!

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, 157 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, 279 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.

4.97 out of 5 average rating, 112 reviews

The living area features a rustic stone fireplace with a modern television mounted above. A chandelier and barn doors enhance the space, while a cozy armchair is positioned near the fireplace. A dining table with four chairs is visible, providing a warm gathering spot.

Townhouse in Winter Park

Rustic Glam Mountain Escape - Near Downtown/Trails

Renovated mountain townhome hosted by experienced, 5-star Superhosts! After exploring nature and enjoying downtown Winter Park, soak your tired legs in the private, indoor hot tub. Kick up your feet, and nestle up in front of the crushed glass fireplace. Enjoy the mountain views and warmth of the afternoon sun in the solar room. Cook a gourmet meal in the brand new granite/stainless steel/marble kitchen. Do it all over again after laying your head down to rest on luxuriously-appointed beds!

4.97 out of 5 average rating, 120 reviews

A spacious living area is bathed in natural light from large windows, featuring a gas fireplace set against a stone backdrop. A comfortable couch provides seating, with a rustic coffee table styled with a chess set. Cozy decor elements, including soft blankets, enhance the inviting atmosphere.

Townhouse in Winter Park

Cozy Modern Cabin w/ Hot Tub - Minutes to Ski Area

Welcome to your modern cabin in the woods, the Bear Cabin. Ideally situated in Rendesvouz, with quick access to downtown Winter Park, Winter Park ski area (free shuttle), and miles of trails. Well-appointed with high-end finishes and a hot tub! Luxurious finishes include a stone fireplace (gas), wide-plank hardwood floors, marble countertops, designer tile, and a hand-hewn beam and mantle. Well-appointed kitchen w/ everything needed for cooking. 2 private bedrooms + loft space with bunk beds.

4.96 out of 5 average rating, 287 reviews

The modern mountain home is showcased against a backdrop of snow-covered terrain and distant mountain peaks. Its angled roof and contemporary design blend seamlessly with the natural surroundings. Large windows reflect the serene landscape, while surrounding trees add to the tranquil winter setting.

Cabin in Grand County

Scandinavian-Inspired Escape: Modern Cabin w/ Spa

Escape to our Modern Mountain Home in Grand County, Colorado, where luxury meets wilderness! Nestled amidst majestic mountains, this Scandinavian-inspired retreat offers the perfect blend of rustic charm and contemporary comfort. Wake up to breathtaking views, with hiking, biking, and skiing right outside your door. Highlights: • Panoramic mountain views • Close to Winter Park & RMNP • Scandinavian-inspired design • Wood-burning fireplace • Private hot tub Grand County Permit #106884

4.97 out of 5 average rating, 117 reviews

A modern living area is highlighted by a comfortable sectional sofa and a square glass coffee table. Floor-to-ceiling windows showcase scenic mountain views, while bright light fills the room. The open layout includes a sleek television mounted on the wall and a glimpse of the dining area.

Flat in Winter Park

Luxury Winter Park Studio*PrivHotTub*Majestic View

Brand New Studio styled in HIP MOUNTAIN CONTEMPORARY in EXCLUSIVE Leland Creek! Perched amongst the aspen trees with spectacular sunset views,you'll never want to leave your own private Hot Tub and Deck!Floor to ceiling windows with stunning mountain views,Room+Board furniture and rustic ski vibe fill the home with a Contemporary Chic style.Private Entrance.Good Pets are welcome.10miles to Granby.18 miles to Grand Lake+Rocky Mountain National Park.DenverInternational airport 1.5 HR.

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.

4.91 out of 5 average rating, 266 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.