Skyway Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Save up to CA $775 when you book a flight and hotel together*
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Top Holiday Package Deals in Skyway

Price found within the past 48 hours. Click for updated prices.
The Timberline Condominiums

The Timberline Condominiums

3 out of 5
per person
Aug. 12 - Aug. 19
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Denver (DEN)
9/10 Wonderful! (744 reviews)
A condo complex that actually has amenities, isn’t run by some offsite slumlord and the description was accurate.

Reviewed on Feb. 13, 2024

The Crestwood Condominiums

The Crestwood Condominiums

3 out of 5
per person
Aug. 12 - Aug. 19
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Denver (DEN)
9.2/10 Wonderful! (288 reviews)
Parking is challenging but the EV charger is free!

Reviewed on Feb. 21, 2024

The Lodge at Vail, A RockResort

The Lodge at Vail, A RockResort

4 out of 5
Save 100% on your flight
per person
Aug. 3 - Aug. 10
found 5 hours ago
Roundtrip flight included
Ottawa (YOW) to Denver (DEN)
8.8/10 Excellent! (1,000 reviews)
Love this place! Even though it was off-season, they were very accommodating and welcoming.

Reviewed on May 5, 2024

Limelight Hotel Snowmass

Limelight Hotel Snowmass

4 out of 5
per person
Aug. 12 - Aug. 19
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Denver (DEN)
9.6/10 Exceptional! (588 reviews)
Spacious room. Clean environment

Reviewed on Apr. 5, 2024

Villas at Snowmass Club

Villas at Snowmass Club

3.5 out of 5
per person
Aug. 12 - Aug. 19
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Denver (DEN)
9.2/10 Wonderful! (217 reviews)
Property is out of date and cleanliness was significantly poor. The master bedroom sheets had dried blood and the pull out couch sheets were dirty as well. Probably won’t come back.

Reviewed on Feb. 18, 2024

Where to stay in Skyway

Find the best Skyway areas and neighborhoods for the activities you enjoy most. Learn more about Skyway
Colorado Springs which includes a park, outdoor art and a fountain

Central Colorado Springs

1 out of top 10 points of interest in this area
4/5(2 area reviews)

While visiting Central Colorado Springs, you might make a stop by sights like United States Olympic Complex and Monument Valley Park.

Find hotel + flight trips in Central Colorado Springs

Skyway Hotel Deals

Cheyenne Mountain Resort, A Dolce by Wyndham
Cheyenne Mountain Resort, A Dolce by Wyndham
4 out of 5
3225 Broadmoor Valley Road, Colorado Springs, CO
Fully refundableReserve now, pay when you stay
The price is CA $208 per night from Jun. 2 to Jun. 3
CA $208
CA $260 total
includes taxes & fees
Jun 2 - Jun 3
8.4/10 Very Good! (1,183 reviews)
Nice Place!
"It was a beautiful lodge with breathtaking views. Very clean, nice staff but short on help."

Reviewed on May 23, 2024

Cheyenne Mountain Resort, A Dolce by Wyndham
The Academy Hotel Colorado Springs
The Academy Hotel Colorado Springs
3.5 out of 5
8110 N Academy Blvd, Colorado Springs, CO
Fully refundableReserve now, pay when you stay
The price is CA $183 per night from Jun. 3 to Jun. 4
CA $183
CA $202 total
includes taxes & fees
Jun 3 - Jun 4
8.8/10 Excellent! (3,008 reviews)
Always a great stay.
"This is our standard reservation when we travel from Texas to Steamboat Springs to visit our daughter. My kids love the indoor pool and free breakfast. Staff is very friendly and the lobby is so nice and relaxing."

Reviewed on May 24, 2024

The Academy Hotel Colorado Springs
Magnuson Grand Pikes Peak
Magnuson Grand Pikes Peak
2.5 out of 5
45 Manitou Ave, Manitou Springs, CO
Fully refundableReserve now, pay when you stay
The price is CA $220 per night from Jun. 3 to Jun. 4
CA $220
CA $244 total
includes taxes & fees
Jun 3 - Jun 4
9.2/10 Wonderful! (1,153 reviews)
"Friendly, clean and enjoyable."

Reviewed on May 25, 2024

Magnuson Grand Pikes Peak
See all 2,971 properties in Skyway
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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Skyway vacation package cost?
Starting from as little as CA $1,764, you can create your own Skyway package the way you want. Simply combine hotels, flights and car rentals and be rewarded with discounts.
How do I get a cheap travel package to Skyway?
Combine your bookings with Expedia to save big bucks on your next getaway. With more than 550 partner airlines and 1,000,000 properties across the globe, your Skyway vacation package can be customized exactly to suit your travel style. With all those extra dollars, why not throw in one or more exciting experiences and tours? It’s an easy way to unlock even more discounts. The vacation you’ve always dreamed of in Skyway is much closer than you thought!
Where should I stay in Skyway?
Make sightseeing a breeze by staying someplace close to Skyway’s main attractions. Pikes Peak and Garden of the Gods are two which top many visitors’ bucket lists.
What are the top hotels in Skyway?
When it comes to welcoming places to stay in Skyway, you can’t go past Modern Home With Koi Pond And Patio. Take a look at its deals and land a great price.
How far in advance should I book my Skyway vacation?
To score rock-bottom prices, book early. Air carriers usually release flight tickets, along with some of the lowest fares, nearly a year prior to departure. Hotels, experiences and car rental should also be booked early to avoid disappointment. If you were hoping for a last-minute getaway in Skyway, there are always plenty of great deals to be had on Expedia. Book your escape today!
What does an Expedia Skyway travel package include?
Flights, rental cars and hotels — you’ll discover them all here. With Expedia, you can create your Skyway package however you want. All you have to do is determine exactly what you need. Once you’ve made your booking, you can add extras like activities and experiences. The more you bundle, the greater your savings!
What should I know before booking a Skyway travel package?
You’ll pick up terrific savings when you bundle your hotels, flights and rental cars into a package. Not just that, booking everything together simply makes planning easier. So why waste money or time? Whether you’re organizing an upscale romantic escape or an affordable family break, browse our vacation packages today.
Can I choose my airline with a Skyway Expedia vacation package?
Expedia offers access to more than 550 airline partners globally, so you sure can! Just pick the carrier that suits you and put together the perfect Skyway escape.
If I'm not able to travel, can I cancel my Skyway vacation package?
Whether it’s your flight or hotel, you can cancel and rebook it. Locked in your Skyway vacation package in the last 24 hours? You may be able to make changes or cancellations for free. For bookings made more than 24 hours ago, you may incur a charge from your airline, hotel or car rental company. For more information, take a look at our Customer Service Portal. We’ll help you each step of the way.

Discover the most popular places to visit in Skyway

Image for Pikes Peak

Pikes Peak

5/5(13 reviews)

The second-most visited mountain in the world is an easy day trip from Colorado’s capital.

Pikes Peak
Image for Garden of the Gods

Garden of the Gods

5/5(18 reviews)

Get a taste for the Colorado landscape as you explore this huge city park on your own or during a guided bus or Segway tour.

Garden of the Gods
Image for US Air Force Academy

US Air Force Academy

4.5/5(4 reviews)

Enjoy a free tour of the military campus where young men and women are trained to be officers in the United States Air Force.

US Air Force Academy

Things to do

Image for Colorado Springs: Garden of the Gods and Foothills Jeep Tour

Colorado Springs: Garden of the Gods and Foothills Jeep Tour

CA $183
Per adult
100% of travellers recommend
Colorado Springs: Garden of the Gods and Foothills Jeep Tour
Image for Colorado Springs: Garden of the Gods Segway Tour

Colorado Springs: Garden of the Gods Segway Tour

CA $186
Per adult
100% of travellers recommend
Colorado Springs: Garden of the Gods Segway Tour
Image for Garden of the Gods 2 Hour Walking Tour

Garden of the Gods 2 Hour Walking Tour

CA $144
Per adult
Garden of the Gods 2 Hour Walking Tour
See all activities in Colorado Springs

Other vacations you might like

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