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 $97 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 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)
LocationFamilyComfort
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).
LocationFamilyQuiet
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
ValueLocationLayout
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.
ValueFamilyCondition
Prime location, amazing views, stylish, sleeps 7
Relax and unwind at this stylish, centrally-located condo. Features include an updated kitchen as well as both bathrooms, a cozy fire place, spacious patio to enjoy morning coffee with incredible views all season. Located just 0.5 miles from downtown Winter Park you can easily walk to restaurants and shops. A shuttle stop to Winter Park Resort is conveniently located just outside the front door making the slopes just minutes away. Easy access to biking/hiking trails as well as Wolf Park.
ValueFamilyCleanliness
Luxury Winter Park Retreat with Private Hot Tub
Welcome to your mountain escape in the heart of Winter Park. This newly built townhome is just 8 minutes from Winter Park Ski Resort, offering the perfect balance of adventure and comfort. After a day on the slopes or trails, unwind in your Private Hot Tub as the mountains glow around you, then head inside to relax by the fireplace with friends and family. With open living spaces, this home was designed for memorable mountain stays. Winter Park Short Term Rental Registration No 029388
LocationValueComfort
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.
ValueLocationSleep quality
Spacious Cabin with Views • Location • Hot Tub
Spacious mountain retreat in Winter Park with sweeping mountain and ski slope views. Minutes to Winter Park Resort, downtown, and Fraser, 30 mins to lakes and under 1hr to Rocky Mountain National Park. Relax in the private hot tub, gather around the fireplace, or enjoy open living with smart TVs, games, heated garage, grill, and outdoor dining. Easy access to hiking, biking and skiing. Comfortably sleeps 10, making it the perfect year-round Colorado getaway for families and groups.
LocationFamilyWi-Fi
Beautiful Condo at Winter Park!
Beautiful one bedroom condo that sleeps up to 6 and situated at one of the best locations at Iron Horse. All amenities including pool, hot tub, fitness center, and garage are in the same building! Walk across the sky bridge and you’re at the corridor run connecting the base of Mary Jane to the base of Winter Park. Condo includes a king, queen Murphy, and one queen plus bed from a new American leather sleeper sofa. Completely equipped kitchen and great place for all activities!
FamilyLocationAir conditioning
Moose House in Perfect Location!
PERFECT LOCATION with a CREEK in the backyard! > Sleeps 13 guests comfortably > 4 bedroom > 3 Baths > 2 Fireplaces > HotTub for 8 > Town square directly across street - restaurants, shops, 2 min. walk. **This property is also perfect for family reunions and small private weddings. For larger groups than 13, there is also a smaller cottage on the same property for rent, which can sleep 3 more guests. Both properties can be rented together. Please contact us to coordinate.
LocationValueAir conditioning
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.
FamilyLocationAmenities
Updated Fraser Condo | Trails, Shuttle & W/D
Bright, comfortable 1-bedroom condo in the heart of Fraser — walking distance to the free shuttle into Winter Park, local trails, shops, and restaurants. The open floor plan makes it easy to relax after a day on the mountain. In-unit washer/dryer, cozy furnishings, and a quiet, well-kept building. A short walk behind the building takes you to the community pond, where you’ll find mountain views and a spot to fish. Perfect home base for skiing, hiking, or just unwinding.
ValueLocationHeating
Popular amenities for Winter Park holiday rentals
Other great holiday rentals in Winter Park
Private 2-acre Mtn Retreat - Hot Tub + Game Room
ValueLocationCleanliness
Winter Park Home | Hot Tub Sauna Walk to Downtown
FamilyLocationIndoor spaces
Luxury Condo on Main Street - Winter Park, CO
FamilyLocationCondition
10 Minute Walk to the Winter Park Gondola 6 beds.
FamilyValueBiking
Chalet Apres | Amazing Location | Hot Tub & Sauna
LocationFamilyCondition
Rooftop Penthouse Vail Luxury Ski-In Ski-Out
LocationValueKitchen
Mountain Retreat | New Condo | Private Hot Tub
LocationFamilyAmenities
Alpine Luxe Loft- Hot Tub, Fireplace, Views, Ski
LocationFamilyKitchen
When is the best time to visit Winter Park?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $365 AUD | $382 AUD | $353 AUD | $276 AUD | $257 AUD | $254 AUD | $268 AUD | $239 AUD | $240 AUD | $249 AUD | $280 AUD | $401 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
- Rentals with pools Winter Park
- Apartment rentals Winter Park
- Family-friendly rentals Winter Park
- Rentals with a kayak Winter Park
- Rentals with an accessible height toilet Winter Park
- House rentals Winter Park
- Ski-in/ski-out rentals Winter Park
- Townhouse rentals Winter Park
- Rentals with a sauna Winter Park
- Luxury rentals Winter Park
- Chalet rentals Winter Park
- Rentals with lake access Winter Park
- Cabin rentals Winter Park
- Condo rentals Winter Park
- Rentals with a hot tub Winter Park
- Pet-friendly rentals Winter Park
- Hotel rooms Winter Park
- Rocky Mountain National Park
- Red Rocks Amphitheatre
- Breckenridge Ski Resort
- Coors Field
- Empower Field at Mile High
- Vail Ski Resort
- City Park
- Ball Arena
- Arapahoe Basin Ski Area
- Colorado Convention Center
- Winter Park Resort
- Beaver Creek Resort
- Loveland Ski Area
- University of Denver
- Pearl Street Mall
- Denver Zoo
- St. Mary's Glacier
- Colorado Cabin Adventures
- Fillmore Auditorium
- Golden Gate Canyon State Park
- Denver Botanic Gardens
- Elitch Gardens
- University Of Colorado Boulder
- Water World