Winter Park Vacations

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Photo by Winter Park Resort

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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
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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 Moffat Tunnel West Portal.

Find hotels in Old Town Winter Park

Find the Best Winter Park Vacation Packages

Winter Park Hotel Deals

The Vintage Hotel
The Vintage Hotel
3 out of 5
100 Winter Park Dr, Winter Park, CO
The price is AED 403 per night from Jun 3 to Jun 4
AED 403
AED 481 total
includes taxes & fees
3 Jun - 4 Jun
8.6/10 Excellent! (1,001 reviews)
"Thank for a lovely stay, where my pet gets to feel like part of the family and is welcomed!"

Reviewed on 26 May 2025

The Vintage Hotel
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 April 2025

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Winter Park Mountain Lodge
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
The price is AED 455 per night from Jun 4 to Jun 5
AED 455
AED 516 total
includes taxes & fees
4 Jun - 5 Jun
8.8/10 Excellent! (689 reviews)
"Comfy bed. Super friendly staff. Wonderful coffee from lobby. Firepit out front is nice spot. It would be nice to add a touch of greenery or screening around the hottubs for privacy. A full length mirror in room would be nice addition."

Reviewed on 16 May 2025

Gravity Haus Winter Park
See all 2,257 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 vacation package cost?
Offering great value package deals on Expedia, you’ll be surprised at how little a vacation 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 vacation packages and you could land some excellent off-season deals.
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 vacation as a package?
You can enjoy significant savings on your next Winter Park getaway by booking a personalized vacation package. Check the “Package” heading, then select your travel dates and destination to view some great airfares and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation 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 accommodations 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 accommodations and airfare: After you’ve settled on your dates and duration, book the right Winter Park vacation package for you.

Discover the most popular places to visit in Winter Park

Winter Park Ski Resort featuring snow skiing, forests and snow

Winter Park Ski Resort

4.5/5(371 reviews)

Hit the slopes at Winter Park Ski Resort, a top ski area in Winter Park. Discover the mountain views in this quaint area.

Winter Park Ski Resort

Trestle Bike Park

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

Trestle Bike Park

The Gondola

4.5/5(6 reviews)

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

The Gondola