Old Town Winter Park Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Kayla Templin

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

While visiting Winter Park Village, you might make a stop by sights like Winter Park Ski Resort and Amaze'n Maze Winter Park.

Find hotels in Winter Park Village

Top hotels in Old Town Winter Park

A Frame Club

A Frame Club

3.5 out of 5
1008 Winter Park Dr Winter Park CO
The price is 6.959.568 ₫ per night from 26 Nov to 27 Nov
6.959.568 ₫
8.922.693 ₫ total
26 Nov - 27 Nov
includes taxes & fees
9/10 Wonderful! (102 reviews)
The staff was great and responsive. I loved the use of text messages to communicate. The grounds were immaculate and after it snowed, someone was out immediately ensuring all the walkways were safe. The town was adorable and this was just what I needed for a mini getaway. I will definitely be ...

Reviewed on 18 Nov 2025

A Frame Club
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
8.4/10 Very Good! (3,489 reviews)
Room was great, lots of pillows and a plush blanket. Bathroom was nice, private toilet inside the bathroom. Front desk was very helpful and polite.

Reviewed on 20 Nov 2025

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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 2.609.838 ₫ per night from 30 Nov to 1 Dec
2.609.838 ₫
4.012.060 ₫ total
30 Nov - 1 Dec
includes taxes & fees
9/10 Wonderful! (4,143 reviews)
Hot tub

Reviewed on 21 Nov 2025

Monarch Casino Resort Spa Black Hawk
See all 3,477 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 holiday 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 holiday package. It's that easy! From hotels and flights to activities and rental cars, Expedia makes travelling cheap and easy. And with more than 550 partner airlines and 1null000null000 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 favourites among many savvy travellers.
How far in advance should I book my Old Town Winter Park holiday?
Travellers 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 holiday 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 holiday 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 holiday package?
Whether it's your hotel, flight or rental car, yes, you can amend or cancel it. Locked in your Old Town Winter Park holiday 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

The Gondola

Enjoy a trip to The Gondola and popular activities such as skiing in Winter Park. Discover the mountain views in this quaint area.

The Gondola

Trestle Bike Park

Enjoy a trip to Trestle Bike Park and popular activities such as skiing in Winter Park. Discover the mountain views in this quaint area.

Trestle Bike Park

Iron Horse Chairlift

Enjoy a trip to Iron Horse Chairlift and popular activities such as skiing in Winter Park. Discover the mountain views in this quaint area.

Iron Horse Chairlift