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*

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

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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.
Motel 6 Aurora, CO – Medical Center

Motel 6 Aurora, CO – Medical Center

2.5 out of 5
City Center
Price was CA $1,011, price is now CA $735 per person
CA $735
per person
Sep 4 - Sep 11
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Denver (DEN)
6/10 (1,005 reviews)
Air conditioning was falling off the wall in unit 160 and in unit 163 the people next door kept going out to smoke constantly and since the smoke tray was next door it reeked of cigarette.

Reviewed on Jul 23, 2026

The Source Hotel

The Source Hotel

4.5 out of 5
Five Points
Price was CA $1,600, price is now CA $1,248 per person
CA $1,248
per person
Sep 23 - Sep 27
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Denver (DEN)
8.8/10 Excellent! (1,010 reviews)
The wifi did not work at all in the hotel room- very frustrating

Reviewed on Jul 28, 2026

The Maven Hotel at Dairy Block

The Maven Hotel at Dairy Block

4.5 out of 5
LoDo
Price was CA $1,554, price is now CA $1,222 per person
CA $1,222
per person
Sep 27 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Denver (DEN)
9.4/10 Exceptional! (1,140 reviews)

Patterson Inn

Patterson Inn

3.5 out of 5
Capitol Hill
Price was CA $1,293, price is now CA $1,018 per person
CA $1,018
per person
Sep 27 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Denver (DEN)
9.6/10 Exceptional! (804 reviews)
Great place! Great breakfast!

Reviewed on Jul 23, 2026

Catbird Hotel

Catbird Hotel

4 out of 5
River North Art District
Price was CA $1,113, price is now CA $890 per person
CA $890
per person
Sep 27 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Denver (DEN)
9.2/10 Wonderful! (1,008 reviews)

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

4 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 $193 per night from Aug 11 to Aug 12
CA $193
CA $231 total
Aug 11 - Aug 12
includes taxes & fees
8.8/10 Excellent! (1,010 reviews)
"This is an older hotel, build in the 1980's but it was well maintained and very clean. We did not use the pool or hot tub but saw plenty of people going in and out. There was a small pantry with a few options for food, like pop tarts ans such, but that was it. The bar attached to the hotel did not ..."

Reviewed on Jul 27, 2026

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 $180 per night from Aug 25 to Aug 26
CA $180
CA $204 total
Aug 25 - Aug 26
includes taxes & fees
Gravity Haus Winter Park
Winter Park Chateau

Winter Park Chateau

4 out of 5
405 Lions Gate Drive Winter Park CO
The price is CA $135 per night from Aug 9 to Aug 10
CA $135
CA $153 total
Aug 9 - Aug 10
includes taxes & fees
9.8/10 Exceptional! (152 reviews)
"John was very responsive and helpful during our stay. We highly recommend this property for location, amenities, and spacious rooms ."

Reviewed on Jul 20, 2026

Winter Park Chateau
See all 2,349 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
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Beach Vacations
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Stay near popular Winter Park attractions

A snowy mountain landscape with ski slopes, a ski lift, and a town in the valley.
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

What to do in Winter Park

YOU Drive the Jeep! Guided 4x4 Tour in Black Hawk

YOU Drive the Jeep! Guided 4x4 Tour in Black Hawk (Denver)

CA $1,348
per traveller
YOU Drive the Jeep! Guided 4x4 Tour in Black Hawk (Denver)
See all activities in Winter Park

Frequently asked questions

How much does a Winter Park vacation package cost?
You'll find cheap prices from CA $735 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.

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