Old Town Winter Park Trips (flight + hotel)

Photo by Kayla Templin

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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
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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

Top hotels in Old Town Winter Park

Ameristar Casino Resort Spa Black Hawk

Ameristar Casino Resort Spa Black Hawk

4 out of 5
111 Richman St Black Hawk CO
Fully refundableReserve now, pay when you stay
The price is P5,934 per night from Jan 21 to Jan 22
P5,934
P8,539 total
Jan 21 - Jan 22
includes taxes & fees
8.4/10 Very Good! (3,570 reviews)
It was great!

Reviewed on Jan 14, 2026

Ameristar Casino Resort Spa Black Hawk
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 P5,742 per night from Jan 21 to Jan 22
P5,742
P8,873 total
Jan 21 - Jan 22
includes taxes & fees
9/10 Wonderful! (4,158 reviews)
The hotel is wonderful

Reviewed on Jan 14, 2026

Monarch Casino Resort Spa Black Hawk
Horseshoe Black Hawk - A Caesars Rewards Destination

Horseshoe Black Hawk - A Caesars Rewards Destination

3 out of 5
401 Main St Black Hawk CO
Fully refundableReserve now, pay when you stay
The price is P5,234 per night from Jan 19 to Jan 20
P5,234
P7,353 total
Jan 19 - Jan 20
includes taxes & fees
7.8/10 Good! (1,124 reviews)
Clean room nice size nice bathroom. It was extremely hot and the beds are a little hard but we will stay there again

Reviewed on Jan 12, 2026

Horseshoe Black Hawk - A Caesars Rewards Destination
See all 3,555 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.

Frequently asked questions

How much does an Old Town Winter Park vacation package cost?
Customize your Old Town Winter Park package from just . 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.

Popular places to visit

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