Holiday houses 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 $99 AUD 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 and kid-friendly amenities
Pet-friendly accommodation
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
Wi-Fi availability
1,650 of Winter Park holiday rentals include Wi-Fi 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.
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)
Zephyr Ski In/Out at Winter Park - 1/2 Price Tues!
Location is everything and this place has it. Right in the heart of the WP Village with views of the Continental Divide and steps to the gondola. The condo has one queen bedroom plus one pull-out couch. Full bathroom with shower/tub combo and a full kitchen with dishwasher. KEY ITEM: There is no dining room table. Meals are at a high-top bar with bar stools, or at the coffee table. Smart TV for streaming and full cable TV in both rooms. Deck has an overhang for extra cover during storms.
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 Rustic Moose
Newly remodeled, 2 bedroom, 2 bath condo with cozy fireplace in Beaver Village. Enjoy the deck surrounded by a beautiful forest view! Steps from the front door is the free Lyft bus to the WP Ski Resort, Fraser and Granby. Walking distance to downtown Winter Park. After a day of fun (skiing, hiking, biking, fishing, and summer concerts) relax and enjoy the pool, 3 hot tubs and sauna at the Clubhouse. Great ski vacation or summer destination. The unit has the rare amenity of a washer and dryer.
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
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.
3 BD/3 BA + BunkRoom + Top Floor Spa + MTN Views
Nestled in the heart of the picturesque Winter Park, Colorado, this exquisite 3-bedroom, 3-bath condo with full size beds bunk room is a perfect mountain retreat that combines rustic charm with modern comforts. Located on the top floor, this corner unit boasts high vaulted ceilings, offering an open and airy atmosphere that's further enhanced by stunning mountain views. Whether you're seeking a cozy winter haven or a refreshing summer escape, this condo promises an unforgettable experience.
Downtown Winter Park W/ Hot Tub
Welcome to your modern mountain retreat, where mountain beauty meets downtown Winter Park's lively charm. This thoughtfully designed home offers the perfect balance of adventure and relaxation. Unwind in the private loft-level hot tub or enjoy the cozy main floor with a gas fireplace and fully equipped kitchen. The loft features a bedroom, office nook, and Murphy bed, plus a wet bar. Located on Main Street, you’re steps from dining, shops, parks, and The Lift shuttle to Winter Park Resort.
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.
Trestle Bike Park•Hot Tub•Pet Friendly•Mtn View
Cozy mountain studio on the Mary Jane Corridor near Trestle Bike Park and Winter Park Village. Perfect for summer mountain biking, hiking, and outdoor adventures. Features a queen bed, sofa bed, full kitchen, electric fireplace, fast Wi Fi, and spacious bathroom with tub and separate shower. Enjoy the outdoor hot tub, gym, free laundry, grill area, trail access, uncovered parking, and pet-friendly accommodations. The Studio doesn’t have AC unit.
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.
Winter Park Studio: On the River~ Walk Downtown!
Fireside Haven is a cozy studio located on a secluded spot RIGHT on the Fraser River, yet is walkable to all that downtown Winter Park has to offer. Dine-out, shop, enjoy coffee at a café, cocktails at happy hour, hike/bike and catch the ski shuttle all within a five-minute walk from your front door! You will have a king-size bed, queen-size sofa sleeper, full kitchen, bathroom, fireplace, private patio & ski closet.
Popular amenities for Winter Park holiday rentals
Other great holiday rentals in Winter Park
Cosmic Cabin: Views, Trails, HotTub by Winter Park
Ramble Retreat I Downtown Winter Park w/Hot Tub
AC, newer 2 Bed / 2 Bath with private Hot tub
492 Mountain Peak Dr.
New 2BD/2BA w/AC: Walk to Restaurants + Shopping!
Luxury Winter Park Retreat with Private Hot Tub
Bright Modern Mountain Getaway | Views + Garage
Beautiful Home Near Everything on Cranmer
When is the best time to visit Winter Park?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $371 AUD | $388 AUD | $359 AUD | $281 AUD | $261 AUD | $258 AUD | $272 AUD | $243 AUD | $244 AUD | $253 AUD | $285 AUD | $408 AUD |
| Avg. temp | -7°C | -7°C | -3°C | -1°C | 4°C | 9°C | 13°C | 12°C | 8°C | 2°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
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- Rocky Mountain National Park
- Red Rocks Amphitheatre
- Breckenridge Ski Resort
- Empower Field at Mile High
- Coors Field
- Vail Ski Resort
- City Park
- Ball Arena
- Arapahoe Basin Ski Area
- Colorado Convention Center
- Keystone Resort
- Beaver Creek Resort
- Winter Park Resort
- Loveland Ski Area
- Granby Ranch
- University of Denver
- Pearl Street Mall
- St. Mary's Glacier
- Denver Zoo
- Ski Cooper
- Golden Gate Canyon State Park
- Colorado Cabin Adventures
- Fillmore Auditorium
- Denver Botanic Gardens