Winding Trail Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • 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 Winding Trail

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
The Highlands
Price was CA $1,626, price is now CA $1,174 per person
CA $1,174
per person
Jul 30 - Aug 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Denver (DEN)
9.6/10 Exceptional! (1,173 reviews)
Beautiful accommodation and friendly staff. Mountain views were terrific!

Reviewed on Jun 10, 2026

Kindred Resort a RockResort

Kindred Resort a RockResort

4 out of 5
River Run
Price was CA $2,266, price is now CA $1,560 per person
CA $1,560
per person
Jul 30 - Aug 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Denver (DEN)
10/10 Exceptional! (2 reviews)
Beautiful property! Great location and staff.

Reviewed on Jun 8, 2026

The Source Hotel

The Source Hotel

4.5 out of 5
Five Points
Price was CA $1,895, price is now CA $1,396 per person
CA $1,396
per person
Aug 12 - Aug 18
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Denver (DEN)
8.8/10 Excellent! (1,010 reviews)
Pool was smaller in person but the deck was great.

Reviewed on Jun 8, 2026

Hotel Polaris

Hotel Polaris

4.5 out of 5
Price was CA $1,774, price is now CA $1,322 per person
CA $1,322
per person
Aug 13 - Aug 18
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Denver (DEN)
9.6/10 Exceptional! (778 reviews)
Property was amazing with friendly staff

Reviewed on Jun 10, 2026

Flying Horse Resort & Club

Flying Horse Resort & Club

4.5 out of 5
Flying Horse
Price was CA $2,115, price is now CA $1,585 per person
CA $1,585
per person
Aug 13 - Aug 18
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Denver (DEN)
9.4/10 Exceptional! (875 reviews)
Very nice property. Decent just outside busy Co Springs. Nice restaurant and bar area. Staff very friendly.

Reviewed on May 28, 2026

Where to stay in Winding Trail

Find the best Winding Trail areas and neighborhoods for the activities you enjoy most. Learn more about Winding Trail
Central Boulder

Central Boulder

5 out of top 10 points of interest in this area
4.5/5(5 area reviews)

If you're spending some time in Central Boulder, Boulder Theater and Pearl Street Mall are top sights worth seeing.

Find hotels in Central Boulder

Winding Trail Hotel Deals

The Westin Westminster

The Westin Westminster

4 out of 5
10600 Westminster Boulevard Westminster CO
Fully refundableReserve now, pay when you stay
The price is CA $187 per night from Jun 19 to Jun 20
CA $187
CA $211 total
Jun 19 - Jun 20
includes taxes & fees
8.8/10 Excellent! (1,120 reviews)
"amazing staff and beautiful space."

Reviewed on Jun 11, 2026

The Westin Westminster
Hotel Boulderado

Hotel Boulderado

4 out of 5
2115 13th St Boulder CO
Fully refundableReserve now, pay when you stay
The price is CA $339 per night from Jun 14 to Jun 15
CA $339
CA $389 total
Jun 14 - Jun 15
includes taxes & fees
9.6/10 Exceptional! (1,745 reviews)
"Great location!"

Reviewed on Jun 11, 2026

Hotel Boulderado
Omni Interlocken

Omni Interlocken

4 out of 5
500 Interlocken Blvd Broomfield CO
Fully refundableReserve now, pay when you stay
The price is CA $322 per night from Jun 12 to Jun 13
CA $322
CA $392 total
Jun 12 - Jun 13
includes taxes & fees
9.2/10 Wonderful! (1,012 reviews)
"The jacuzzi was broken the entire time. The food was good at the restaurant and the staff were friendly. The property was beautiful - wish we could’ve taken advantage of all of it. Spa closed on Monday and Tuesday also quite inconvenient."

Reviewed on Jun 11, 2026

Omni Interlocken
See all 1,774 properties in Winding Trail
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 a Winding Trail vacation package cost?
Choose from any combination of flights, hotels and car rentals, and you can be vacationing in Winding Trail from just CA $1,174. And the more you bundle, the more money you save. Your dream vacation has never been more affordable.
How do I get a cheap travel package to Winding Trail?
Our Winding Trail vacation packages mean plenty of savings for the savvy explorer. For the best deals, simply combine your hotel, flights and extras (such as activities) into a handy package. But bargain prices are just the beginning of your next amazing adventure. Book with Expedia and you'll have more than 550 air carriers and 1,000,000 properties across the globe to select from. No matter your budget or style, there's a vacation package that's perfect for you.
Where should I stay in Winding Trail?
A visit to Winding Trail isn't complete without stopping by University of Colorado Boulder and Folsom Field. Stay nearby and easily access these impressive sights.
How far in advance should I book my Winding Trail vacation?
To score rock-bottom prices, book ASAP. Airlines typically begin selling tickets, along with some of the lowest fares, around a year in advance. Hotels, experiences and car rental should also be booked well in advance to avoid disappointment. If you're in need of a last-minute getaway to Winding Trail, there are always plenty of great deals on Expedia. Book your escape today!
What does an Expedia Winding Trail travel package include?
With Expedia, you can select any combination of hotels, flights and car rentals to create your perfect Winding Trail package. Once you've made your booking, you can add on all the fun stuff like tours and activities. Remember, the more you bundle, the more deals you'll score!
What should I know before booking a Winding Trail travel package?
So many places to explore, so many things to do. With a package, you'll be able to afford more of them. Bundle your hotels, flights and rental cars and land big savings.
Can I choose my airline with a Winding Trail Expedia vacation package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines globally. Our packages give you the freedom to take your pick of available flights, hotels and activities that suit you.
If I'm not able to travel, can I cancel my Winding Trail vacation package?
Don't stress if you're rethinking your Winding Trail vacation package — it's possible to change or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur fees from your airline, hotel or car rental company. We get that life can occasionally throw a spanner in the travel works, so head to our Customer Service Portal if that occurs. When you're ready to make changes, we'll take care of it.

Discover the most popular places to visit in Winding Trail

Pearl Street Mall

Pearl Street Mall

4/5(19 reviews)

Shop, dine or simply enjoy the atmosphere of Boulder's busy downtown shopping quarter. Relax by flower-filled gardens and let your children splash in the fountains.

Pearl Street Mall
Chautauqua Park

Chautauqua Park

4/5(6 reviews)

Embark on gentle or rigorous hikes and photograph native wildlife at this popular city park. See cultural performances and learn about a historic education movement.

Chautauqua Park

Colorado Chautauqua

You can find out about the history of Boulder when you stop by Colorado Chautauqua. Discover the area's shops, or seek out its biking trails.

Colorado Chautauqua

Things to do

Picture 14 for Activity Boulder: Best of Boulder eBike Tour – City to Foothills

Boulder: Best of Boulder eBike Tour – City to Foothills

CA $145
per adult
Boulder: Best of Boulder eBike Tour – City to Foothills
Rocky Mountains: Peak to Peak & Estes Park Small Group Tour

Rocky Mountains: Peak to Peak & Estes Park Small Group Tour

CA $179
per adult
Rocky Mountains: Peak to Peak & Estes Park Small Group Tour
See all activities in Boulder
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.