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 $90 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 Cabin w/ Hot Tub & Garage - Minutes to Mtn
2BR townhome with a loft in a woodsy neighborhood in Winter Park/Fraser. Want a relaxing scenic place to sit by the fire or enjoy Grand County's outdoor adventures? Come stay and enjoy this townhome with access to free shuttle transportation during the winter. Both bedrooms include King beds. The loft includes a daybed that expands to a king bed and the sofa pulls out to a bed. PRIVATE 7 PERSON HOT TUB on patio. Propane Grill, easy access to hiking/biking trails, restaurants, stores, bars, etc.
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.
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)
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).
Cosmic Cabin: Views, Trails, HotTub by Winter Park
Escape to the tranquility of our uniquely designed home, embraced by the trees. With viewing windows in every space, including a solarium perfect for stargazing, you’ll feel immersed in nature’s beauty. Set on an acre of forest w/ direct access to trails for hiking, biking, cross-country skiing and snowshoeing. Just 15 minutes from Winter Park Ski Resort and close to town, yet peacefully secluded. Enjoy the huge hot tub, four decks, miles of trails and endless opportunities to unwind in nature.
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.
Homebase Snowblaze
Enjoy the magic of the Fraser River Valley and charm of downtown Winter Park from our well-equipped, completely remodeled studio. Only an hour and thirty minute drive from Denver International Airport. Walking distance to Winter Park's Main St. lined with shops and dining and a quick 5 minute drive to the world class slopes of Winter Park resort. Take advantage of the free "Lift" bus, with a stop right out front of the building and a ride to the resort in less than 5 minutes. WP STR # 009036.
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.
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.
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
Popular amenities for Winter Park holiday rentals
Other great holiday rentals in Winter Park
Cozy Summer Getaway | Luxury Condo in Downtown
Lodge 212 | Brand New LUXE Designer Home + Hot Tub
Trestle Bike Park•Hot Tub•Pet Friendly•Mtn View
Luxury Condo on Main Street - Winter Park, CO
A-Frame | 15 min to Winter Park | Private Acre
Mountain Condo w/ Hot Tub | Walk to Town | Ski Bus
Mountain Cozy | New w/ Hot Tub
New 2BD/2BA w/AC: Walk to Restaurants + Shopping!
When is the best time to visit Winter Park?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $337 SGD | $353 SGD | $326 SGD | $217 SGD | $204 SGD | $215 SGD | $247 SGD | $221 SGD | $222 SGD | $229 SGD | $259 SGD | $371 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
- Rentals with a firepit Winter Park
- Flat rentals Winter Park
- Rentals with an EV charger Winter Park
- Family-friendly rentals Winter Park
- Rentals with a kayak Winter Park
- Rentals with a fireplace 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
- Rentals with a patio Winter Park
- Apartment rentals Winter Park
- Rentals with a hot tub Winter Park
- Pet-friendly rentals Winter Park
- Fitness-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
- Arapahoe Basin Ski Area
- Colorado Convention Center
- Ball Arena
- Beaver Creek Resort
- Winter Park Resort
- Loveland Ski Area
- Granby Ranch
- Pearl Street Mall
- University of Denver
- Ski Cooper
- Denver Zoo
- St. Mary's Glacier
- Fillmore Auditorium
- Golden Gate Canyon State Park
- Denver Botanic Gardens
- Elitch Gardens
- Colorado Cabin Adventures