Winding Trail Vacations

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Your Winding Trail Vacation

Make planning your travels easy by booking a vacation package to Winding Trail. Let us handle the specifics, so you can focus on enjoying everything this neighborhood can offer. When it's time to explore the sights, you'll find loads of top attractions nearby including University of Colorado Boulder, Folsom Field and Pearl Street Mall. Visit one, two (or even all!) during your trip to Winding Trail. Whatever your travel goals or the size of your budget, booking your ideal Winding Trail vacation is simple with Expedia.

The Latest Winding Trail Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Rocky Mountain Hotel & Conference Center

Rocky Mountain Hotel & Conference Center

3 out of 5
Save 100% on your flight
per person
Aug 10 - Aug 13
found 1 day ago
Roundtrip flight included
San Antonio (SAT) to Denver (DEN)
6.8/10 (2,123 reviews)
Back entry doors wouldn’t unlock with keys, had to walk around front. Then other guests started blocking the doors open with a rock. When i asked the staff, they were aware of this situation.

Reviewed on Jun 21, 2024

The Historic Crag's Lodge

The Historic Crag's Lodge

3 out of 5
Save 100% on your flight
per person
Aug 10 - Aug 13
found 1 day ago
Roundtrip flight included
San Antonio (SAT) to Denver (DEN)
8.8/10 Excellent! (1,012 reviews)
Cool historic inn Great staff Dining looked good although we were unable to eat there Good sunset location at the pool

Reviewed on Jun 19, 2024

WorldMark Estes Park

WorldMark Estes Park

3.5 out of 5
Save 100% on your flight
per person
Aug 10 - Aug 13
found 1 day ago
Roundtrip flight included
San Antonio (SAT) to Denver (DEN)
9.2/10 Wonderful! (109 reviews)
Beautiful condo room. Loved being on lower level by the river. Was put in an ada which was not needed but still nothing to be bothered about. All appliances were awesome and functioning. Couldn't figure out how to use the dvd player but again not a big deal! Would love to have had a firepit out off our patio but again, no big deal! I think our biggest issue was check out time! Waaay to early. 11:00 am is early but pretty much the standard and we thought it was 11:00am until we got a phone call right about 10:00 am and had to scramble, no showers, no breakfast to get out in time without any extra charges. Other than that, it was a great stay!

Reviewed on May 17, 2024

The Gant

The Gant

4 out of 5
East Aspen
per person
Aug 1 - Aug 4
found 1 day ago
Roundtrip non-stop flight included
San Antonio (SAT) to Denver (DEN)
9.4/10 Exceptional! (763 reviews)
Excellent service. Five star! Kids loved the pool and hot tub. So did the adults. In the heart of Aspen.

Reviewed on Jun 18, 2024

Aspen Meadows Resort

Aspen Meadows Resort

4 out of 5
per person
Aug 1 - Aug 4
found 1 day ago
Roundtrip non-stop flight included
San Antonio (SAT) to Denver (DEN)
9/10 Wonderful! (694 reviews)
Amazing grounds, located close to downtown Aspen, and very relaxing. Staff/maid service was top notch. Worth a look for anyone wanting to stay in Aspen without all the crowded areas.

Reviewed on Apr 30, 2024

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

Central Boulder

7 out of top 10 points of interest in this area
4.5/5(433 area reviews)

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

Find hotel + flight trips 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 $159 per night from Jun 23 to Jun 24
$159
$180 total
includes taxes & fees
Jun 23 - Jun 24
9.4/10 Exceptional! (1,208 reviews)
"Wonderful experience whenever we go back to Colorado would definitely stay there again"

Reviewed on Jun 19, 2024

Hotel Boulderado
The Westin Westminster
The Westin Westminster
4 out of 5
10600 Westminster Boulevard, Westminster, CO
The price is $124 per night from Jun 23 to Jun 24
$124
$140 total
includes taxes & fees
Jun 23 - Jun 24
8.6/10 Excellent! (1,095 reviews)
"Nice!"

Reviewed on Jun 19, 2024

The Westin Westminster
Omni Interlocken
Omni Interlocken
4 out of 5
500 Interlocken Blvd, Broomfield, CO
Fully refundableReserve now, pay when you stay
The price is $203 per night from Jul 12 to Jul 13
$203
$250 total
includes taxes & fees
Jul 12 - Jul 13
8.6/10 Excellent! (1,001 reviews)
"Very pleasant check in."

Reviewed on Jun 20, 2024

Omni Interlocken
See all 1,607 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly 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 $416. 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

Image for University of Colorado Boulder

University of Colorado Boulder

4.5/5(1,401 reviews)

Enjoy the collegiate vibe around University of Colorado Boulder, a top college in Boulder. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

University of Colorado Boulder
Image for Pearl Street Mall

Pearl Street Mall

4.5/5(1,272 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
Image for Chautauqua Park

Chautauqua Park

4.5/5(455 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

Things to do

Image for Highlights of Boulder, Colorado Walking Tour

Highlights of Boulder, Colorado Walking Tour

$245
Per adult
Highlights of Boulder, Colorado Walking Tour
Image for Best of Boulder E-Bike Tour

Best of Boulder E-Bike Tour

$104
Per adult
100% of travellers recommend
Best of Boulder E-Bike Tour
Image for Ride Boulder's Best Guided eBike Tour

Ride Boulder's Best Guided eBike Tour

$110
Per adult
Ride Boulder's Best Guided eBike Tour
See all activities in Boulder

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