Winter Park Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Winter Park Resort

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
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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.

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Top hotels in Winter Park

The Vintage Hotel
The Vintage Hotel
3 out of 5
100 Winter Park Dr, Winter Park, CO
The price is 3.314.386 ₫ per night from 29 Jun to 30 Jun
3.314.386 ₫
3.954.486 ₫ total
29 Jun - 30 Jun
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"My kids and I loved this hotel! Only downfall was no AC but it gets pretty cold at night so I would put the fan in the window to get the nice cool breeze in our room to cool it which worked perfectly and I kept the blinds closed during the day. The pool and spa were really nice as well, the bricks ..."

Reviewed on 24 Jun 2025

The Vintage Hotel
Gravity Haus Winter Park
Gravity Haus Winter Park
3.5 out of 5
78869 US-40, Winter Park, CO
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (695 reviews)
"Simple, comfortable, great location & staff"

Reviewed on 23 Jun 2025

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Gravity Haus Winter Park
Winter Park Mountain Lodge
Winter Park Mountain Lodge
3 out of 5
81699 US Highway 40, Winter Park, CO
6.4/10 (1,000 reviews)
"Great location and price, Our room was clean, Employees were nice and helpful. Downside was no breakfast was offered and the pool and hot tub were not working. Property could use some updates. Overall I will stay here again."

Reviewed on 24 Apr 2025

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Winter Park Mountain Lodge
See all 2,274 properties in Winter Park
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.

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?

  1. 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.
  2. 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.
  3. 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.
  4. Combine your accommodation and airfare: After you've settled on your dates and duration, book the right Winter Park holiday package for you.

Popular places to visit

Trestle Bike Park

Enjoy a trip to Trestle Bike Park and popular activities such as skiing in Winter Park. Discover the mountain views in this quaint area.

Trestle Bike Park

The Gondola

Enjoy a trip to The Gondola and popular activities such as skiing in Winter Park. Discover the mountain views in this quaint area.

The Gondola

The Fraser River Trail

Enjoy a trip to The Fraser River Trail and popular activities such as skiing in Winter Park. Discover the mountain views in this quaint area.

The Fraser River Trail