Old Town Winter Park Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • 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

Top Holiday Package Deals in Old Town Winter Park

Price found within the past 48 hours. Click for updated prices.
The Green Mountain Falls Lodge

The Green Mountain Falls Lodge

3 out of 5
Price was CA $1,522, price is now CA $1,054 per person
CA $1,054
per person
Sep 4 - Sep 11
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Denver (DEN)
8.4/10 Very good! (294 reviews)
The property was clean, the hotel room was clean but the shower base was not. What disappointed me the most was the swimming pool was across the street and was open to the public. I shouldn’t pay $200 for just a room. The pool didn’t look like the picture and it should state that it was not part of the property and open to the public!!! Total disappointment

Reviewed on Aug 3, 2026

Glenwood Springs Inn

Glenwood Springs Inn

2 out of 5
Downtown
Price was CA $1,675, price is now CA $1,140 per person
CA $1,140
per person
Sep 14 - Sep 19
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Denver (DEN)
8.8/10 Excellent! (1,602 reviews)

Patterson Inn

Patterson Inn

3.5 out of 5
Capitol Hill
Price was CA $2,845, price is now CA $2,033 per person
CA $2,033
per person
Sep 15 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Québec (YQB) to Denver (DEN)
9.6/10 Exceptional! (807 reviews)

Hotel Jerome, Auberge Collection

Hotel Jerome, Auberge Collection

5 out of 5
Downtown Aspen
Price was CA $7,804, price is now CA $5,662 per person
CA $5,662
per person
Sep 4 - Sep 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Denver (DEN)
9.6/10 Exceptional! (477 reviews)

Hotel Teatro

Hotel Teatro

4.5 out of 5
Downtown Denver
Price was CA $2,711, price is now CA $2,065 per person
CA $2,065
per person
Sep 17 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
Québec (YQB) to Denver (DEN)
9/10 Wonderful! (1,385 reviews)
The staff were uniformly welcoming, and

Reviewed on Aug 5, 2026

Where to stay in Old Town Winter Park

Find the best Old Town Winter Park areas and neighborhoods for the activities you enjoy most. Learn more about Old Town 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

Old Town Winter Park Hotel Deals

A Frame Club

A Frame Club

4 out of 5
1008 Winter Park Dr Winter Park CO
The price is CA $369 per night from Aug 27 to Aug 28
CA $369
CA $480 total
Aug 27 - Aug 28
includes taxes & fees
9.2/10 Wonderful! (116 reviews)
"Property was super cute with the A style home. Outdoors was so beautiful. The river was so pretty as well. Great layout and hot tubs were very relaxing. Inside the home it was clean but some things could be cleaner. The couch had dog hairs, some silverware had stains, the shampoo/conditioner bottles ..."

Reviewed on Jul 19, 2026

A Frame Club
New Ground Level Riverfront Suite - Walk to Village!

New Ground Level Riverfront Suite - Walk to Village!

Winter Park CO
9.6/10 Exceptional! (139 reviews)
"The place was nice and spacious. Unfortunately we couldn't cook on the BBQ grill. We brought food to do just that. The grill was filthy inside and out."

Reviewed on Jul 16, 2026

Get rates
New Ground Level Riverfront Suite - Walk to Village!
Monarch Casino Resort Spa Black Hawk

Monarch Casino Resort Spa Black Hawk

4 out of 5
488 Main St Black Hawk CO
The price is CA $189 per night from Aug 24 to Aug 25
CA $189
CA $273 total
Aug 24 - Aug 25
includes taxes & fees
Monarch Casino Resort Spa Black Hawk
See all 3,521 properties in Old Town 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

Frequently asked questions

How much does an Old Town Winter Park vacation package cost?
Customize your Old Town Winter Park package from just CA $1,054. Choose from any combination of flights, hotels and rental cars to craft the getaway you've been dreaming about. Don't forget to add on some tours and experiences!
How do I get a cheap travel package to Old Town Winter Park?
Search for flights that suit your schedule, add a hotel room to your booking and watch the savings stack up with an Old Town Winter Park vacation package. It's that easy! From hotels and flights to activities and rental cars, Expedia makes traveling cheap and easy. And with more than 550 partner airlines and 1,000,000 properties worldwide to select from, you'll never be short of choice.
Where should I stay in Old Town Winter Park?
Most who travel to Old Town Winter Park include University of Colorado Boulder and Folsom Field on their sightseeing itineraries. Why not reserve a hotel right near these popular attractions?
What are the top hotels in Old Town Winter Park?
If it's your very first time in Old Town Winter Park, reserve a room at Trademark Condo Short Walk To Shuttle By Redawning or Slopeside Sanctuary - Penthouse < 1 Mi To Lifts. Both offer comfortable beds and are favorites among many savvy travelers.
How far in advance should I book my Old Town Winter Park vacation?
Travelers are generally able to browse international airfares on Expedia up to a year in advance of departure. Booking at the last minute? With a stroke of luck, it's still possible to score a cheaper ticket only weeks before your flight.
What does an Expedia Old Town Winter Park travel package include?
Packages include hotels, rental cars and flights, but you can mix and match them to create your ideal Old Town Winter Park trip. You can also add on experiences and activities once you've made your booking. You're in control! When you bundle your bookings with Expedia, you'll enjoy discounts you won't find elsewhere.
What should I know before booking an Old Town Winter Park travel package?
Locking in all the parts of your getaway together is one of the best ways to save. Combine your car rentals, flights and hotels into a handy package. But you're not limited to hotels. Expedia has all sorts of properties, including vacation rentals such as oceanfront condos and city apartments. Your choices are almost endless!
Can I choose my airline with an Old Town Winter Park Expedia vacation package?
You can, and with over 550 airlines to pick from all over the world, you have plenty of choice. Search the available options and see which airline fits your budget and needs.
If I'm not able to travel, can I cancel my Old Town Winter Park vacation package?
Whether it's your hotel, flight or rental car, yes, you can amend or cancel it. Locked in your Old Town Winter Park vacation package in the last 24 hours? You may be able to make any changes for free. For older bookings, you may be charged a fee by your hotel, airline or car rental company. For further information, take a look at our Customer Service Portal. We're here to help you each step of the way.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.