Winding Trail Vacation Packages

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Top Holiday Package Deals in Winding Trail

Price found within the past 48 hours. Click for updated prices.
Wingate by Wyndham Greenwood Village/Denver Tech

Wingate by Wyndham Greenwood Village/Denver Tech

2.5 out of 5
Denver Tech Center
Price was CA $992, price is now CA $705 per person
CA $705
per person
Sep 28 - Oct 5
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Denver (DEN)
8.2/10 Very Good! (1,004 reviews)
Just what I was looking for

Reviewed on Aug. 15, 2025

Hotel Polaris

Hotel Polaris

4.5 out of 5
Price was CA $1,706, price is now CA $1,101 per person
CA $1,101
per person
Oct 2 - Oct 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Denver (DEN)
9.6/10 Exceptional! (310 reviews)
Like that Parking was free. Loved the hotel decor. The suite we stayed in was beautiful. Restaurants was expensive.

Reviewed on Aug. 21, 2025

Hampton Inn Denver West Federal Center

Hampton Inn Denver West Federal Center

2.5 out of 5
Union Square
Price was CA $1,076, price is now CA $719 per person
CA $719
per person
Sep 28 - Oct 5
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Denver (DEN)
8.8/10 Excellent! (1,008 reviews)
Excellent breakfast pool, and service

Reviewed on Aug. 17, 2025

The Parker Hotel

The Parker Hotel

3.5 out of 5
Price was CA $1,293, price is now CA $871 per person
CA $871
per person
Oct 24 - Oct 31
found 4 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Denver (DEN)
9.2/10 Wonderful! (854 reviews)
Place has a great vibe. No negatives!

Reviewed on Aug. 18, 2025

Basecamp Boulder

Basecamp Boulder

3.5 out of 5
Central Boulder
Price was CA $1,136, price is now CA $807 per person
CA $807
per person
Oct 2 - Oct 6
found 7 hours ago
Roundtrip flight included
Edmonton (YEG) to Denver (DEN)
8.8/10 Excellent! (1,002 reviews)
Very friendly staff, super helpful about the area

Reviewed on Aug. 15, 2025

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
Boulder featuring a sunset and kayaking or canoeing as well as a large group of people

Central Boulder

6 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

Hotel Boulderado

Hotel Boulderado

3.5 out of 5
2115 13th St, Boulder, CO
Fully refundableReserve now, pay when you stay
The price is CA $207 per night from Aug 24 to Aug 25
CA $207
CA $238 total
Aug 24 - Aug 25
includes taxes & fees
9.4/10 Exceptional! (1,504 reviews)
"Historic property with vintage charm. Very close to dining options, like the biergarten, and the hotel bar had a great selection of drinks and food that was open late after the concert we attended. Would definitely stay here again!"

Reviewed on Aug. 19, 2025

Hotel Boulderado
DoubleTree by Hilton Denver - Westminster

DoubleTree by Hilton Denver - Westminster

4 out of 5
8773 Yates Dr, Westminster, CO
Fully refundableReserve now, pay when you stay
The price is CA $124 per night from Aug 31 to Sep 1
CA $124
CA $138 total
Aug 31 - Sep 1
includes taxes & fees
7.2/10 Good! (1,002 reviews)
"Extremely comfortable beds, self parking, on site restaurant, indoor pool"

Reviewed on Aug. 19, 2025

DoubleTree by Hilton Denver - Westminster
Origin Westminster a Wyndham Hotel

Origin Westminster a Wyndham Hotel

3.5 out of 5
8875 WESTMINSTER BLVD, Westminster, CO
Fully refundableReserve now, pay when you stay
The price is CA $136 per night from Aug 28 to Aug 29
CA $136
CA $152 total
Aug 28 - Aug 29
includes taxes & fees
9/10 Wonderful! (1,014 reviews)
Perfect for a small intimate gathering
"Had a wonderful time!. The room was clean and exactly what we needed for the night. Also the water pressure in the shower was to die for. Will stay again when I need a small getaway night."

Reviewed on Aug. 19, 2025

Origin Westminster a Wyndham Hotel
See all 1,625 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 $705. 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 featuring mountains

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

Rocky Mountain National Park Hiking

Rocky Mountain National Park Hiking

CA $246
per traveller
98% of travellers recommend
Rocky Mountain National Park Hiking
Astronomy Tour

Astronomy Tour

CA $62
per adult
Astronomy Tour
Scenic Mountain Photoshoot in Boulder, Colorado

Scenic Mountain Photoshoot in Boulder, Colorado

CA $172
per traveller
Scenic Mountain Photoshoot in Boulder, Colorado
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.