Winter Park Vacation Packages

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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.
Hyatt Vacation Club at The Ranahan

Hyatt Vacation Club at The Ranahan

4 out of 5
Northside Breck
Price was CA $1,196, price is now CA $753 per person
CA $753
per person
Oct 12 - Oct 18
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Denver (DEN)
9.6/10 Exceptional! (1,453 reviews)
We love this place so much! We've stayed here a couple of times already and we're looking forward to coming back next year!

Reviewed on Aug. 28, 2025

Patterson Inn

Patterson Inn

3.5 out of 5
Capitol Hill
Price was CA $1,387, price is now CA $875 per person
CA $875
per person
Nov 7 - Nov 11
found 5 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Denver (DEN)
9.6/10 Exceptional! (738 reviews)
Great property with great service.

Reviewed on Aug. 19, 2025

Beaver Run Resort & Conference Center

Beaver Run Resort & Conference Center

3.5 out of 5
Peak 9
Price was CA $1,202, price is now CA $792 per person
CA $792
per person
Oct 12 - Oct 18
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Denver (DEN)
8.4/10 Very Good! (1,010 reviews)
Everything is excellent except to find your builiding #, room #. Suites had an excellent view of mountains.

Reviewed on Aug. 27, 2025

Gold Point Resort Breckenridge by Vacatia

Gold Point Resort Breckenridge by Vacatia

3 out of 5
Baldy Mountain
Price was CA $1,298, price is now CA $889 per person
CA $889
per person
Oct 12 - Oct 18
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Denver (DEN)
9.2/10 Wonderful! (104 reviews)
Great mountain views. Great layout and spacious. Kitchen was perfectly equipped, appliances pretty new. Loved the fireplace. Bus picks up right at the resort and takes takes you right to the gondola to ski. Negatives: Hot tub in the building was under filled and not very clean. Beds are very stiff.

Reviewed on Mar. 20, 2025

The Crawford Hotel

The Crawford Hotel

5 out of 5
LoDo
Price was CA $1,664, price is now CA $1,155 per person
CA $1,155
per person
Nov 13 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Denver (DEN)
9.2/10 Wonderful! (1,004 reviews)
Good central stay. Staff are lovely. Recommend asking for a room that doesn’t t overlook the station though - that was the only thing I didn’t like, thankfully the sound proofing worked perfectly and we didn’t hear a single train.

Reviewed on Aug. 25, 2025

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.

Find hotels in Old Town Winter Park

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 $162 per night from Aug 31 to Sep 1
CA $162
CA $194 total
Aug 31 - Sep 1
includes taxes & fees
8.6/10 Excellent! (1,010 reviews)
"We went to the winter park Tacos and Margs festival. The Vintage Hotel was great for location and a great night sleep with mountain air."

Reviewed on Aug. 25, 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
The price is CA $136 per night from Sep 29 to Sep 30
CA $136
CA $154 total
Sep 29 - Sep 30
includes taxes & fees
Gravity Haus Winter Park
A Frame Club

A Frame Club

3.5 out of 5
1008 Winter Park Dr, Winter Park, CO
The price is CA $342 per night from Aug 31 to Sep 1
CA $342
CA $464 total
Aug 31 - Sep 1
includes taxes & fees
A Frame Club
See all 2,297 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
Family Vacations
Family Vacations

Discover the most popular places to visit in Winter Park

Winter Park Ski Resort showing snow skiing, landscape views and mountains

Winter Park Ski Resort

With seven ski territories, summer sports, spas, diverse restaurants and live music, this is one of Colorado’s most complete mountain resorts.

Winter Park Ski Resort

Amaze'n Maze Winter Park

Enjoy a trip to Amaze'n Maze Winter Park and popular activities like skiing in Winter Park. Discover the mountain views in this quaint area.

Amaze'n Maze Winter Park

Frequently asked questions

How much does a Winter Park vacation package cost?
You'll find cheap prices from CA $753 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.

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