Winding Trail Vacation Packages

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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The Latest Winding Trail Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Outdoor spa tub
    Jul 30 - Aug 4

    Hyatt Vacation Club at The Ranahan + Flight

    The Highlands
    5 nights
    4.0 star property
    9.6/10 - Exceptional (1,191 reviews)
    "Beautiful accommodation and friendly staff. Mountain views were terrific!"
    Reviewed June 10, 2026
    Roundtrip • Toronto (YYZ) - Denver (DEN)
    YYZ - DEN • 1 stop DEN - YYZ • 1 stop
    CA $1,626
    CA $1,174
    per traveller
    found 18 hours ago
    Hyatt Vacation Club at The Ranahan
  • 55-inch TV with cable channels, Netflix, streaming services
    Jul 30 - Aug 4

    Kindred Resort a RockResort + Flight

    River Run
    5 nights
    4.0 star property
    10/10 - Exceptional (3 reviews)
    "Beautiful property! Great location and staff."
    Reviewed June 8, 2026
    Roundtrip • Toronto (YYZ) - Denver (DEN)
    YYZ - DEN • 1 stop DEN - YYZ • 1 stop
    CA $2,266
    CA $1,560
    per traveller
    found 18 hours ago
    Kindred Resort a RockResort
  • Exterior
    Aug 13 - Aug 18

    Hotel Polaris + Flight

    Colorado Springs
    5 nights
    4.5 star property
    9.6/10 - Exceptional (789 reviews)
    "Property was amazing with friendly staff"
    Reviewed June 10, 2026
    Roundtrip • Toronto (YYZ) - Denver (DEN)
    YYZ - DEN • Nonstop DEN - YYZ • Nonstop
    CA $1,774
    CA $1,322
    per traveller
    found 1 day ago
    Hotel Polaris
  • 2 outdoor pools, open 9:00 AM to 8:00 PM, pool umbrellas, sun loungers
    Aug 13 - Aug 18

    Flying Horse Resort & Club + Flight

    Flying Horse
    5 nights
    4.5 star property
    9.4/10 - Exceptional (876 reviews)
    "Very nice property. Decent just outside busy Co Springs. Nice restaurant and bar area. Staff very friendly."
    Reviewed May 28, 2026
    Roundtrip • Toronto (YYZ) - Denver (DEN)
    YYZ - DEN • Nonstop DEN - YYZ • Nonstop
    CA $2,114
    CA $1,585
    per traveller
    found 1 day ago
    Flying Horse Resort & Club
  • Front of property
    Aug 17 - Aug 21

    The Brown Palace Hotel and Spa, Autograph Collection + Flight

    Downtown Denver
    4 nights
    4.5 star property
    8.4/10 - Very good (1,002 reviews)
    "Built in 1892, the Brown Palace has seen better days. The bathroom sink had cracks that encompassed the bowl. The ceiling had several patches of paint ready to fall, in addition to stains. One curtain rod was partially snapped off. There were few amenities i.e. shower cap. Staff processed my bill incorrectly. This is a Marriott BonVoy property."
    Reviewed June 10, 2026
    Roundtrip • Edmonton (YEG) - Denver (DEN)
    YEG - DEN • 1 stop DEN - YEG • 1 stop
    CA $2,087
    CA $1,584
    per traveller
    found 12 hours ago
    The Brown Palace Hotel and Spa, Autograph Collection

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 $208 per night from Jun 20 to Jun 21
CA $208
CA $234 total
Jun 20 - Jun 21
includes taxes & fees
8.8/10 Excellent! (1,119 reviews)
"The hotel was welcoming and inviting the staff was excellent! The room was clean and very comfortable. Very soft sheets great pillows room service was quick and food was hot when delivered. I enjoyed my stay. Also they have a great walking park behind the hotel. I will definitely be staying there ..."

Reviewed on Jun 8, 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! (1,011 reviews)
"Sweet spot. Will happily return."

Reviewed on Jun 10, 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 . 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.