Winter Park Holidays
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Where to stay in Winter Park
Find the best Winter Park areas and neighborhoods for the activities you enjoy most. Learn more about Winter Park
Winter Park Village
3 out of top 10 points of interest in this area
While visiting Winter Park Village, you might make a stop by sights like Winter Park Ski Resort and The Gondola.
Old Town Winter Park
If you're looking for some top things to see and do in Old Town Winter Park and surrounding area, you can visit Winter Park Ski Resort and Trestle Bike Park.
Hideaway Village South
While there might not be top attractions in Hideaway Village South, you can explore the larger area and discover places like Blue Sky Massage and Bella Vita.
Hideaway Junction
While Hideaway Junction isn't home to many top sights, Cozens Ranch House Museum and Grand Park Community Recreation Center are some notable places to visit nearby.
Hideaway Village
When in Hideaway Village, you can plan a visit to Blue Sky Massage and Bella Vita, some noteworthy sights in the nearby area.
Top hotels in Winter Park
The Vintage Hotel
100 Winter Park Dr Winter Park CO
S$195
26 Aug - 27 Aug
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
"The staff was super friendly. Free parking was a bonus. We got the kitchenette and loved it."
Reviewed on 12 Aug, 2026
Gravity Haus Winter Park
78869 US-40 Winter Park CO
Fully refundableReserve now, pay when you stay
S$192
13 Sept - 14 Sept
includes taxes & fees
Winter Park Chateau
405 Lions Gate Drive Winter Park CO
S$163
16 Aug - 17 Aug
includes taxes & fees
9.8/10 Exceptional! (156 reviews)
"Great family stay with all the comforts of home. Great location, food, and hosts. Hope to come back in the winter to enjoy the mountain."
Reviewed on 11 Aug, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Stay near popular Winter Park attractions
Photo by Winter Park Resort
Winter Park Ski Resort
9.4/10 (1,284 reviews)
Just 90 minutes from Denver, Winter Park Resort offers 3,000 acres of diverse terrain for every skill level. Take the first chair for freshly groomed trails during legendary Colorado powder days.
The Gondola
9.2/10 (249 reviews)
Ascend to 10,700 feet on Winter Park's scenic gondola for panoramic views of the Fraser Valley and Continental Divide. At the summit, explore hiking trails or savour mountain cuisine at Sunspot Mountaintop Lodge.
The Fraser River Trail
9.2/10 (26 reviews)
The Fraser River Trail connects Fraser and Winter Park through Colorado's mountain landscapes with scenic river views. Enjoy a leisurely 5-mile journey past meadows where moose and deer often make surprise appearances.
Trestle Bike Park
8.4/10 (99 reviews)
America's largest full-service downhill bike park offers 40+ miles of lift-served trails through stunning alpine terrain. Riders of all levels can enjoy everything from flowy beginner runs to technical expert lines.
Challenger Chair Lift
9.0/10 (28 reviews)
Enjoy a trip to Challenger Chair Lift and popular activities such as skiing in Winter Park. Discover the mountain views in this quaint area.
Iron Horse Chairlift
8.8/10 (45 reviews)
This historic 1974 chairlift connects Winter Park and Mary Jane ski areas with a scenic 13-minute mountain ascent. Enjoy diverse terrain while taking in panoramic Rocky Mountain views.
Village Cabriolet
8.8/10 (171 reviews)
This open-air gondola whisks you between Winter Park's parking area and village base in just two minutes. Enjoy panoramic mountain views while comfortably transporting all your gear for free.
Blue Sky Massage
7.4/10 (31 reviews)
Enjoy a trip to Blue Sky Massage and popular activities such as skiing in Winter Park. Discover the mountain views in this quaint area.
What to do in Winter Park
Idaho Springs: Clear Creek Ziplining Experience
S$135
per adult
100% of travellers recommend
Half Day Fly Fishing Lesson on Clear Creek near Denver
S$387
per adult
Denver/Black Hawk: You-Drive Jeep Tour in the Backcountry
S$773
per traveller
Frequently asked questions
How much does a Winter Park holiday package cost?
Offering great value package deals on Expedia, you'll be surprised at how little a holiday to Winter Park costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Winter Park?
You can typically find lower rates and better availability in May, October and November. Explore our cheap Winter Park holiday packages and you could land some excellent off-season deals.
How many days is enough for Winter Park?
With about 2 days, you'll have enough time to enjoy popular neighbourhoods like Old Town Winter Park and Bear Crossing during your Winter Park holiday. Be sure to also add Trestle Bike Park and The Fraser River Trail to your must-see list. Looking for more adventures? Consider exploring outside of Winter Park on tours and day trips.
Is it worth booking a holiday package to Winter Park?
Winter Park is a good holiday destination with attractions like Trestle Bike Park among the many things to keep you busy. Whether you're heading away with the family or getting away with friends, a Winter Park holiday promises fun for everyone.
How to find the best Winter Park package deals?
Begin your search for a Winter Park package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select a few filters, like "Property type" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the ideal Winter Park package deal straight away, just switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Winter Park adventure underway.
Is it cheaper to book a Winter Park holiday as a package?
You can enjoy significant savings on your next Winter Park getaway by booking a personalised holiday package. Check the "Package" heading, then select your travel dates and destination to view some great airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a holiday package to Winter Park?
If you have your Winter Park travel dates locked in, book as soon as you can to bag some terrific deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spontaneous getaways? Our last-minute deals are perfect for quick escapes.
How to plan a trip to Winter Park?
- Choose your travel dates: The things you want to do in Winter Park and your preferred season will help you decide when to get away.
- Calculate your budget: Make sure you have enough money to pay for everything from meals and transportation to activities and airfares. Your accommodation will probably be the biggest expense during your trip to Winter Park.
- Work out your trip length: Consider how long you'd like to spend discovering Winter Park. Plan your days so you can get to all the activities and attractions you're interested in at a leisurely pace.
- Combine your accommodation and airfare: After you've settled on your dates and duration, book the right Winter Park holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
