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)
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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.
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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
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Rooftop Penthouse Vail Luxury Ski-In Ski-Out
Discover Winter Park’s most elevated stay. Designed to rival Aspen or Vail luxury, this designer penthouse for four offers floor-to-ceiling views of the slopes and mountains, a rooftop patio, steam shower/sauna, Japanese soaking tub, two fireplaces, and a 100” TV. A floating glass yoga studio and spa-like ensuite provide a true getaway for the mind and body. Enjoy a chef's kitchen with an imported AGA oven, Monogram appliances, an indoor pizza oven, butler’s pantry, and walnut/marble finishes.
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Winter Park Home | Hot Tub Sauna Walk to Downtown
Escape to Ramble On, a pet friendly luxury wellness retreat in downtown Winter Park for 10. - Unwind in your private rooftop hot tub & barrel sauna after a day on the slopes, just a 5-min drive or free shuttle away. - This 4-bed mountain-modern home features a theater room, chef's kitchen, and stunning views. - Perfect for families & groups seeking style and adventure, steps from the Fraser River and local shops. - Tap the ❤ in the upper-right corner to add Ramble On to your wishlist!
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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.
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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
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Duplex In town! Views! PrvtHottub,2Cgarage,Sleeps9
BEST location!! In-town duplex has spectacular mountain views from the deck and plenty of space for multiple families, sleeps 9. Easy access to trailheads and the free Lift shuttle from the front door. Private hot tub, 2 living rooms, 3 bedrooms with en suite bathrooms, full size washer and dryer, main level entrance, gas BBQ, and 2 car garage with 220 outlet for EV charging plus free/easy parking next to house. Just 1 mile to Hideaway Park for easy access to restaurants and shopping!
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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.
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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.
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Ramble Retreat I Downtown Winter Park w/Hot Tub
Immerse yourself in mountain luxury at this stunning multi-story retreat in the heart of Winter Park. Enjoy panoramic views from the rooftop deck, unwind in the private hot tub, or gather around the fire pit after a day of adventure. Featuring beautiful designer, and pet-friendly accommodations, this home offers the perfect blend of comfort and style. Just steps from downtown Winter Park, Hideaway Park, popular restaurants, and year-round festivals and live music events.
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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.
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Popular amenities for Winter Park holiday rentals
Other great holiday rentals in Winter Park
Luxe 4BR Winter Park Retreat w/ Private Hot Tub
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The Rustic Moose
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Luxurious Mountain Home near Downtown Winter Park!
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River Cabin
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Mountain Cozy | New w/ Hot Tub
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Private 2-acre Mtn Retreat - Hot Tub + Game Room
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The Camping Bear
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10 Minute Walk to the Winter Park Gondola 6 beds.
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When is the best time to visit Winter Park?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $333 SGD | $348 SGD | $321 SGD | $252 SGD | $234 SGD | $232 SGD | $244 SGD | $218 SGD | $219 SGD | $227 SGD | $256 SGD | $366 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
- Flat 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
- 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
- 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
- University Of Colorado Boulder
- Elitch Gardens
- Water World