Winding Trail Vacations from $220

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Your Winding Trail Vacation

Your next great escape is calling your name with a vacation package to Winding Trail. Entertainment, relaxation and great times — you're sure to find it in this neighborhood. Not sure what to do during your trip to Winding Trail? Nearby attractions such as University of Colorado Boulder, Folsom Field and Pearl Street Mall are good places to begin. Don't just wish for it — do it! Book your ultimate Winding Trail vacation with Expedia and experience travel your way.

The Latest Winding Trail Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Horseshoe Black Hawk - A Caesars Rewards Destination

Horseshoe Black Hawk - A Caesars Rewards Destination

3 out of 5
Price was $529, price is now $220 per person
$220
per person
Jan 8 - Jan 12
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Denver (DEN)
16/10 Exceptional! (1,045 reviews)
No player rewards and very little security

Reviewed on Nov 25, 2025

Hyatt Vacation Club at The Ranahan

Hyatt Vacation Club at The Ranahan

4 out of 5
Northside Breck
Price was $1,067, price is now $487 per person
$487
per person
Jan 9 - Jan 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Denver (DEN)
19.2/10 Exceptional! (1,598 reviews)
Perfect for a getaway

Reviewed on Nov 24, 2025

Lady Luck Casino Black Hawk

Lady Luck Casino Black Hawk

3 out of 5
Price was $655, price is now $306 per person
$306
per person
Feb 2 - Feb 8
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Denver (DEN)
15.2/10 Exceptional! (1,813 reviews)
Clean room, friendly staff, and ample parking. The room was too cold and offered no working temperature unit.

Reviewed on Nov 22, 2025

Glenwood Springs Inn

Glenwood Springs Inn

2 out of 5
Downtown
Price was $926, price is now $446 per person
$446
per person
Jan 1 - Jan 8
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Denver (DEN)
17.6/10 Exceptional! (1,488 reviews)
The mattress wasn’t in good condition and no soap in the shower

Reviewed on Nov 24, 2025

Luxe Osprey

Luxe Osprey

3 out of 5
Arrowhead
Price was $5,255, price is now $2,600 per person
$2,600
per person
Jan 1 - Jan 4
found 9 hours ago
Roundtrip flight included
Dallas (DFW) to Denver (DEN)
No reviews

Black Friday Sale

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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

6 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 hotels in Central Boulder

Winding Trail Hotel Deals

Hyatt Place Denver/Westminster

Hyatt Place Denver/Westminster

3 out of 5
6865 West 103rd Avenue Westminster CO
Fully refundableReserve now, pay when you stay
$97 nightly
The price is $108 total per night from Nov 30 to Dec 1
$108 total
Nov 30 - Dec 1
Total with taxes and fees
9.2/10 Wonderful! (1,091 reviews)
Great stay

Reviewed on Nov 24, 2025

Hyatt Place Denver/Westminster
Hotel Boulderado

Hotel Boulderado

4 out of 5
2115 13th St Boulder CO
Fully refundableReserve now, pay when you stay
$132 nightly
The price is $152 total per night from Nov 26 to Nov 27
$152 total
Nov 26 - Nov 27
Total with taxes and fees
9.4/10 Exceptional! (1,621 reviews)
Good old fashioned quality!

Reviewed on Nov 20, 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
$86 nightly
The price is $96 total per night from Dec 2 to Dec 3
$96 total
Dec 2 - Dec 3
Total with taxes and fees
7.4/10 Good! (1,005 reviews)
Renovating hot tub and pool with no notice on their website. Wouldn’t have booked if that information was provided.

Reviewed on Nov 18, 2025

DoubleTree by Hilton Denver - Westminster
See all 1,734 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
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Beach Vacations
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Kid Friendly Vacations

Discover the most popular places to visit in Winding Trail

University of Colorado Boulder

University of Colorado Boulder

Explore the campus of University of Colorado Boulder, during your trip to Boulder. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

University of Colorado Boulder
Pearl Street Mall featuring a fountain

Pearl Street Mall

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 which includes mountains

Chautauqua Park

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

Astronomy Tour

Astronomy Tour

$45
per adult
Astronomy Tour
1-Hour Private Scenic Mountain Photoshoot in Boulder

Scenic Mountain Photoshoot in Boulder, Colorado

$125
per traveler
Scenic Mountain Photoshoot in Boulder, Colorado
The Psycho Killer Escape Room

The Psycho Killer Escape Room (1-8 people)

$31
per adult
The Psycho Killer Escape Room (1-8 people)
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.