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 $89 SGD 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.
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)
Mountain Getaway - Hot Tub & Sauna. Dogs welcome!
Escape to our luxury Colorado mountain retreat with stunning Continental Divide views! Comfortably sleeps 8. Features a chef's kitchen, indoor 6-person hot tub & 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.
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).
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
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.
Winter Park home new listing
This newly available, gorgeous, light-filled 4 bedroom 3 1/2 bath home in Rendezvous sleeps up to 10 people. Breathtaking Views of Winter Park & Byers Peak 7 min to Winter Park town center Short drive to the slopes Hot tub 2 car garage with Tesla charger Washer dryer New construction (built in 2022) 2 rooms with King beds and en-suite bathrooms 1 Queen bed 2 bunk beds (4 twin beds) Big screen tv with cable & wifi Nearby hiking trails Outdoor deck with couch, dining table, and gas grille
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
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.
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.
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.
Downtown Mtn Oasis + Hot Tubs | Steps to Events
Escape to the mountains in this beautifully renovated 2-story condo 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
Popular amenities for Winter Park holiday rentals
Other great holiday rentals in Winter Park
The Camping Bear
Private 2-acre Mtn Retreat - Hot Tub + Game Room
Chalet Apres | Amazing Location | Hot Tub & Sauna
Winter Park Ski Resort - Top Floor
Luxury Condo on Main Street - Winter Park, CO
Trestle Bike Park•Hot Tub•Pet Friendly•Mtn View
Trail Side Cabin with Mtn Views & Private Hot Tub
Winter Park Home | Hot Tub Sauna Walk to Downtown
When is the best time to visit Winter Park?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $334 SGD | $350 SGD | $323 SGD | $253 SGD | $235 SGD | $233 SGD | $245 SGD | $219 SGD | $220 SGD | $228 SGD | $257 SGD | $367 SGD |
| 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
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- Family-friendly rentals Winter Park
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- Rentals with an accessible-height toilet Winter Park
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- Ski-in/ski-out rentals Winter Park
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- Rentals with a sauna Winter Park
- Luxury rentals Winter Park
- Chalet rentals Winter Park
- Rentals with lake access Winter Park
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- Apartment 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
- Beaver Creek Resort
- Winter Park Resort
- Loveland Ski Area
- University of Denver
- Pearl Street Mall
- St. Mary's Glacier
- Denver Zoo
- Colorado Cabin Adventures
- Fillmore Auditorium
- Golden Gate Canyon State Park
- Denver Botanic Gardens
- Elitch Gardens
- University Of Colorado Boulder
- Water World