Winter Park Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Winter Park Resort

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Winter Park Vacation

Experience the unique personality of Winter Park with a customized Winter Park vacation package. From its ski fields to its spectacular views and beyond, you'll never have a boring moment in this city. Fill your free time with tours of Winter Park Ski Resort, Trestle Bike Park and The Fraser River Trail, some of the attractions you simply have to see during a trip to Winter Park. Whoever you're taking time off with and whatever you plan to spend, your ultimate Winter Park vacation is just clicks away with Expedia.

Top Winter Park Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Springs Condominiums by Vail Resorts

The Springs Condominiums by Vail Resorts

4 out of 5
River Run
Price was CA $2,052, price is now CA $1,416 per person
CA $1,416
per person
Jan 13 - Jan 18
found 24 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Denver (DEN)
7.8/10 Good! (16 reviews)
Great family oriented resort. The kids loved the pool and slide. We appreciated the on-site BBQ. We'll definitely be back for more.

Reviewed on Jun 30, 2026

Bluegreen Vacations Streamside at Vail, an Ascend Collection Resort

Bluegreen Vacations Streamside at Vail, an Ascend Collection Resort

4.5 out of 5
West Vail
Save 100% on your flight
Price was CA $4,756, price is now CA $3,449 per person
CA $3,449
per person
Dec 28 - Jan 3
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Denver (DEN)
9/10 Wonderful! (119 reviews)

Eagle Point Resort

Eagle Point Resort

4 out of 5
Matterhorn Village
Save 100% on your flight
Price was CA $3,201, price is now CA $2,328 per person
CA $2,328
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Denver (DEN)
8.6/10 Excellent! (618 reviews)

Timbers & Lone Eagle by Vail Resorts

Timbers & Lone Eagle by Vail Resorts

4 out of 5
River Run
Price was CA $2,625, price is now CA $1,920 per person
CA $1,920
per person
Jan 13 - Jan 18
found 24 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Denver (DEN)
9.2/10 Wonderful! (66 reviews)

Hotel Jerome, Auberge Collection

Hotel Jerome, Auberge Collection

5 out of 5
Downtown Aspen
Save 100% on your flight
Price was CA $7,387, price is now CA $5,440 per person
CA $5,440
per person
Dec 5 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Denver (DEN)
9.6/10 Exceptional! (485 reviews)
This lived up to what i had heard. The staff was incredible; the breakfast was top-notch, and the massages were super enjoyable. Great getaway

Reviewed on Oct 18, 2026

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
A snow-covered mountain range with dense forests in the foreground.

Winter Park Village

5 out of top 10 points of interest in this area

If you're spending some time in Winter Park Village, Winter Park Ski Resort and The Gondola are top sights worth seeing.

Find hotels in Winter Park Village

Ready to book your vacation to Winter Park?

 

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Winter Park Hotel Deals

The Vintage Hotel

The Vintage Hotel

3 out of 5
100 Winter Park Dr Winter Park CO
The price is CA $140 per night from Oct 28 to Oct 29
CA $140
CA $167 total
Oct 28 - Oct 29
includes taxes & fees
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
The price is CA $139 per night from Oct 29 to Oct 30
CA $139
CA $158 total
Oct 29 - Oct 30
includes taxes & fees
Gravity Haus Winter Park
Fraser Crossing Founders Pointe

Fraser Crossing Founders Pointe

3.5 out of 5
670 Winter Park Dr Winter Park CO
The price is CA $237 per night from Oct 28 to Oct 29
CA $237
CA $283 total
Oct 28 - Oct 29
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
"We checked in at 8pm after a long drive and never got a code to get into our room till 10:20 pm called, text, drive around for 2 hours. Finally at 10pm we had to check in at a different hotel because no one was helping us and it was late and our child needed to go to bed. They refused to give a refund ..."

Reviewed on Oct 26, 2026

Fraser Crossing Founders Pointe
See all 2,307 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
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Stay near popular Winter Park attractions

A snow-covered ski area sign with a ski symbol, surrounded by snow-laden trees and a clear blue sky.
Photo by Winter Park Resort
Open Photo by Winter Park Resort

Winter Park Ski Resort

9.4/10 (1,284 reviews)
With seven ski territories, summer sports, spas, diverse restaurants and live music, this is one of Colorado’s most complete mountain resorts.
See properties

Frequently asked questions

How much does a Winter Park vacation package cost?
You'll find cheap prices from CA $1,416 on Expedia for your Winter Park getaway. However, factors like the length of stay, hotel choice and season will influence how much your vacation to Winter Park costs.
What are the cheapest months to go to Winter Park?
May, October and November are great times to look for cheap Winter Park vacation packages. Opting to travel in quieter periods means you can generally find lower prices on hotels and flights.
How many days is enough for Winter Park?
Winter Park vacations come in various shapes and sizes, but to get a real feel for this destination, we think 2 days is about right. With this timeframe, you can fit in top sights like Grand Park Community Recreation Centre and Amaze'n Maze Winter Park and seek out some lesser-known spots. Don't forget to visit neighbourhoods such as Old Town Winter Park and Bear Crossing either. If you're clever with your time, you can even take a day trip from Winter Park too.
Is it worth booking a vacation package to Winter Park?
Winter Park has everything you need for an amazing trip. Begin your Winter Park vacation on a high note by visiting top attractions like Trestle Bike Park.
How to find the best Winter Park package deals?
Finding a cheap Winter Park package deal is a cinch with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your budget, apply a couple of filters and browse what's available. You can personalize your search by "Amenities," "Property type," "Traveller experience" and more. Sort the results by "Price: low to high" to view the most economical Winter Park package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are typically lower.
Is it cheaper to book a Winter Park vacation as a package?
You can enjoy significant savings on your Winter Park getaway by booking a personalized vacation package. Click on the "Package" heading, then select your travel dates and destination to see some great airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Winter Park?
If you've got your Winter Park vacation dates locked in, book as soon as you can to snap up some fantastic deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for quick escapes.
How to plan a trip to Winter Park?

  1. Choose the right time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to travel to Winter Park.
  2. Budget wisely: Besides the cost of your hotel, you should factor in other expenses too. These include food, transportation and flights. Also, set aside some extra funds for unexpected costs that could arise during your trip to Winter Park.
  3. Decide how long to go away for: Now that you're more familiar with Winter Park, you can figure out the perfect length of your vacation. Put together a draft plan and give yourself enough time for all the things you want to do.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, hotels, car rental and more into a customized Winter Park vacation package.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.