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Holiday rentals in Winter Park

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Quick stats about holiday rentals in Winter Park

  • Total holiday rentals

    Explore 1,660 holiday rentals in Winter Park

  • Nightly prices starting at

    Winter Park holiday rentals start at €62 per night before taxes and fees

  • Verified guest reviews

    Over 50,060 verified reviews to help you choose

  • Family-friendly holiday rentals

    1,260 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 270 rentals that welcome pets

  • Holiday rentals with a pool

    480 properties feature pools

  • Rentals with dedicated workspaces

    980 properties have a dedicated workspace

  • Wifi availability

    1,650 of Winter Park holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Self check-in, Gym and BBQ grill across Winter Park rentals

  • 4.8 Average rating

    Winter Park stays are highly rated by guests – averaging 4.8 out of 5!

Top-rated holiday rentals in Winter Park

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
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)

4.97 out of 5 average rating, 203 reviews
Guest favourite
The rustic cabin exterior is framed by tall aspen trees and features a wooden door. Bright flower boxes, filled with white and red blooms, add a pop of color in front of the porch area. A grill is positioned nearby on the deck.
Cabin in Winter Park

Cozy Cabin in Perfect Location

You've found the perfect cabin for your trip to Winter Park. Cozy, w/a queen bed & a single, pull-out couch. Small kitchen or -on a nice day- grill on back deck near creek. Electric fireplace adds ambiance. Tiny kitchen w/appliances, Keurig &dishes. STEPS away from Cooper Creek Town Square restaurants & Hideaway Park’s concerts. The City of Winter Park has trains going through the town, which adds to the charm. We love pets/dogs! 2 or more dogs require extra $10 per dog one-time cleaning fee.

4.84 out of 5 average rating, 659 reviews
Guest favourite
Flat in Winter Park

Sleeper@SnowBlaze! Great Location! Hot Tubs/Pool!

Town of Winter Park license (007884) Newly renovated studio in Snowblaze Condominiums! Perfect location in the Town of Winter Park, close to Winter Park Resort and bus stop outside the front door, and walking distance from all the shops, restaurants, and bars in town! Super comfy Queen size bed in a large studio apartment, large couch and ottoman with huge TV! Updated amenities for the community! Pool has been refinished, new outdoor fire pit area, access to gym and community areas included.

4.93 out of 5 average rating, 135 reviews
Top guest favourite
A private balcony features a round table surrounded by four wicker chairs, offering expansive views of the Fraser Valley and mountains. Sunlight illuminates the area, and the nearby river reflects the clear sky.
Apartment in Fraser

View • Fireplace • Hot Tub • Sauna • Pool

Welcome to our favorite place in the mountains We've been sharing our family getaway with guests for years; there's nothing we love more than hearing that someone watched the sunrise with a cup of coffee on the deck, came back from skiing to relax by the fireplace, or spent the evening laughing around the table together We hope you'll feel right at home here And yes...we're dog people🐾 We know vacations are better when the whole family comes along, so well-behaved dogs are warmly welcomed

4.98 out of 5 average rating, 337 reviews
Top guest favourite
A spacious living area features large windows that provide views of the mountains and natural light. Comfortable leather seating surrounds a low coffee table, with a decorative area rug enhancing the space. A warm ambiance is created by a nearby lamp and wooden elements.
Townhouse in Winter Park

Winter Park Townhome w/ Stunning Slope Views!

Experience Winter Park from an unbeatable location directly across from Winter Park Resort. Framed by stunning slope views, this beautifully appointed 3-bed/2.5-bath mountain retreat offers more than 1,800 square feet of spacious living for up to 8 guests. Spend your days skiing world-class terrain, hiking scenic trails, or exploring Winter Park’s dining, breweries, and live music, then return to the comfort of your own mountain escape. Winter Park Short-Term Rental Registration No. 005732

4.94 out of 5 average rating, 163 reviews
Top guest favourite
The exterior of a charming European-style home is displayed, featuring multiple windows with green shutters. A balcony adorned with vibrant flower boxes complements the rustic architecture. Lush greenery surrounds the property, enhancing its inviting appearance against a clear blue sky.
Guest suite in Winter Park

Charming Suite in Old Town Winter Park

Charming European suite steps away from a major ski resort. Located in the heart of Old Town Winter Park this beautiful European Country home is a welcoming retreat for mountain visitors. OUR LARGE PRIVATE SUITE IS IN THE LOWER LEVEL OF OUR HOME, complete with separate bedroom, kitchenette, hot tub, bathroom/shower & FREE PARKING! Take a 10-15 minute walk or short bus ride to the base of the Winter Park Resort to experience incredible skiing and boarding at any of the Resort's Territories.

4.98 out of 5 average rating, 499 reviews
Top guest favourite
A welcoming outdoor entryway features a covered porch with colorful hanging flower baskets. Two chairs are positioned next to a small table, inviting relaxation. A decorative rug adorns the area, complementing the wooden structure and surrounding greenery.
Guest suite in Fraser

Madge’s Studio Pets welcome!

Whether it be play time or quiet time (or both!), we offer our guests (and pets) the comfort of a large studio and yard at the end of a dead end street. You have a beautiful mountain setting with easy access to all your favorite summer activities. In addition, we are 45 minutes from Rocky Mountain National Park and the lakes of Grand Lake. After enjoying a perfect Colorado day, come back to your spacious room for a drink on your private patio to think about what restaurant to enjoy.

4.97 out of 5 average rating, 507 reviews
Top guest favourite
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.

4.97 out of 5 average rating, 135 reviews
Top guest favourite
A private balcony is showcased with a bright blue Adirondack chair and a grill, providing a view of the serene river and surrounding autumn foliage. The warm wooden siding of the property contrasts beautifully with the clear blue sky and distant mountains.
Apartment in Fraser

Walk to Restaurants! Enjoy Cool Fall Days!

Fall is the perfect time to enjoy the mountains! Bike, hike and fish before the snow starts to fly!! Spacious 1 BR Fraser condo perfectly located for your fall 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.

4.97 out of 5 average rating, 150 reviews
Guest favourite
The modern kitchen features a large wooden dining table surrounded by white chairs, with panoramic windows offering expansive views of the mountains and forest. A sleek black appliance suite, including an oven and coffee maker, complements the space, while natural light fills the room.
Cabin in Tabernash

Mountain Getaway - Sauna, Dogs welcome!

Escape to our luxury Colorado mountain retreat with stunning Continental Divide views! Comfortably sleeps 8. Features a chef's kitchen, sauna, and wood-burning fireplace. Family-friendly with a bunk room and travel crib. Just 15 mins to Winter Park Ski Resort & 30 mins to Rocky Mountain National Park in summer months. Perfect for adventure and relaxation. We love dogs and they’re welcome in our home! Please make sure to add them to the booking so we know they’re coming.

4.91 out of 5 average rating, 262 reviews
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

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

4.88 out of 5 average rating, 221 reviews
Top guest favourite
Apartment in Winter Park

Downtown Mtn Oasis + Hot Tubs | Steps to Events

Escape to the mountains in this beautifully renovated 2-story condo (1200 sq. ft.) in the heart of downtown Winter Park. Cozy up by the fireplace, relax in the hot tubs, or take in breathtaking views from your private balcony. Enjoy shops, dining, and live events just steps away, plus a free shuttle stop right nearby for a quick 5-minute ride to Winter Park Resort. Adventure and convenience are at your doorstep! STR License #018230

4.96 out of 5 average rating, 114 reviews

Popular amenities for Winter Park holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Winter Park's top sights

Winter Park Resort

515 locals recommend

Fraser Tubing Hill

219 locals recommend

Colorado Adventure Park

90 locals recommend

Winter Park Pub

44 locals recommend

Grand Adventures

40 locals recommend

Doc's Roadhouse

15 locals recommend

Other great holiday rentals in Winter Park

Top guest favourite
Home in Winter Park

Winter Park Home | Hot Tub Sauna Walk to Downtown

5.0 out of 5 average rating, 20 reviews
Guest favourite
Home in Winter Park

New Luxury Mountain Home | Hot Tub | 3 Fireplaces

5.0 out of 5 average rating, 6 reviews
Top guest favourite
Flat in Winter Park

Mountain Condo w/ Hot Tub | Walk to Town | Ski Bus

5.0 out of 5 average rating, 22 reviews
Top guest favourite
Home in Fraser

Private 2-acre Mtn Retreat - Hot Tub + Game Room

4.98 out of 5 average rating, 42 reviews
Top guest favourite
A spacious living area features a large sectional sofa adorned with blue and yellow cushions. Tall windows provide views of the mountains, while a ceiling fan hangs above. A soft area rug complements the room's neutral color palette, adding warmth to the inviting space.
Apartment in Winter Park

Luxury Condo on Main Street - Winter Park, CO

4.99 out of 5 average rating, 82 reviews
Top guest favourite
The spacious living area features a stone fireplace, surrounded by comfortable seating with colorful cushions. A modern kitchen is visible in the background, showcasing wooden cabinetry and stainless steel appliances. Natural light floods in from large windows, enhancing the welcoming atmosphere.
Townhouse in Winter Park

The Camping Bear

4.92 out of 5 average rating, 79 reviews
Guest favourite
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.
Apartment in Winter Park

10 Minute Walk to the Winter Park Gondola 6 beds.

4.94 out of 5 average rating, 69 reviews
Guest favourite
Townhouse in Winter Park

Luxury Winter Park Retreat with Private Hot Tub

4.97 out of 5 average rating, 36 reviews

When is the best time to visit Winter Park?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price€231€242€223€175€163€161€170€151€152€157€177€254
Avg. temp-7°C-7°C-3°C-1°C4°C9°C13°C12°C8°C2°C-3°C-7°C

Frequently Asked Questions

  • What are the best places to stay in Winter Park?

    Winter Park has inviting neighborhoods near ski slopes, scenic mountain views, and easy trail access. Many visitors choose to stay around the resort area or in town for walkable dining, shopping, and outdoor activities.

  • What are the best things to do in Winter Park with kids?

    Families frequently enjoy sledding, snow tubing, and exploring playgrounds in the winter. In warmer seasons, mini-golf, adventure parks, and guided nature walks are often suggested for younger travelers.

  • What are some of the best things to do in Winter Park?

    Explore the slopes at Winter Park Resort, hike scenic trails, and experience mountain biking or fishing in alpine lakes. Art galleries, local shops, and seasonal festivals add variety throughout the year.

  • How is the weather in Winter Park?

    Winter Park has cold, snowy winters with temperatures ranging from 11 to 36°F (-11 to 2°C), while summer afternoons warm to 62–68°F (17–20°C). Spring and fall are cooler and may bring brief rain or scattered snow.

  • When is the best time to visit Winter Park?

    Winter Park is frequently suggested in winter for skiing and snowboarding, while summer attracts mountain bikers, hikers, and festival goers. Spring and fall bring quieter trails and crisp mountain air.

  • What are the best places to visit in Winter Park?

    Travelers often explore Winter Park Resort, stroll through Hideaway Park, and wander the town’s local art galleries. Seasonal farmers markets and community spaces are also popular gathering spots.

  • What are some hiking trails in Winter Park?

    Winter Park has several frequently suggested hiking trails, including the Fraser River Trail, Jim Creek Trail, and trails around Berthoud Pass. Alpine forests, wildflowers, and broad mountain views make hiking a favorite activity.

  • What are some family activities we can do in Winter Park?

    Families can explore scenic bike paths, visit adventure parks, and try out nearby wildlife watching areas. Guided tours, fishing experiences, and seasonal community events bring people together year round.

  • What are some of the best day trip ideas from Winter Park?

    Day trips from Winter Park often include exploring mountain lakes, small towns with historic main streets, or natural hot springs tucked in scenic valleys. Outdoor parks and wildlife areas around the region are also popular.

  • Are there any pet friendly accommodations available in Winter Park?

    Winter Park has pet-friendly vacation rentals in neighborhoods near the resort, main street, and park areas. Many hosts welcome dogs, and outdoor trails make it easy to explore with your companion.

  • What are some local tips for visiting Winter Park?

    Layer clothing for changing mountain weather, and bring sunscreen for high-altitude sun. Exploring early in the day is often recommended for quieter trails and wildlife sightings.

  • What is Winter Park known for?

    Winter Park is known for its ski resort, mountain biking terrain, and vibrant outdoor recreation. Seasonal festivals, art spaces, and alpine scenery make it a favorite destination for adventurers.

  • What are the best hidden gems to explore in Winter Park?

    Wander quiet trails near local creeks, discover tucked-away parks, or seek out small art galleries and coffee shops just off the main street. Lesser-known fishing spots and forested picnic areas reward curious explorers.

  • What are the best foods to try in Winter Park?

    Try locally inspired dishes such as hearty chili, Rocky Mountain trout, and fresh baked pies in area cafes. In winter, warming stews and hot cocoa are frequently suggested favorites.

  • What should I bring for a trip to Winter Park?

    Bring layers for temperature changes, sturdy shoes for outdoor activities, and sunscreen for higher elevations. In winter, pack gloves, a warm hat, and waterproof gear for snow sports.

  • What is the nightlife in Winter Park like?

    Winter Park has lively bars, casual lounges, and venues hosting local music around the town center. Après-ski gatherings and group-friendly restaurants create a relaxed evening atmosphere.

  • What are the most popular events or festivals in Winter Park?

    Winter Park has recurring music festivals, mountain bike races, and art fairs, often anchored around summer weekends and winter holidays. Seasonal celebrations bring live entertainment and local flavor to community spaces.

  • Are there family friendly vacation rentals in Winter Park?

    Winter Park has a range of family-friendly vacation rentals near town, ski lifts, and recreation areas. Many spaces include additional amenities and flexible layouts for groups traveling with children.

Destinations to explore