Winding Trail Vacation Packages

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  • Better together

    Save up to CA $1,096 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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Top Holiday Package Deals in Winding Trail

Price found within the past 48 hours. Click for updated prices.
Highline Vail - a DoubleTree by Hilton

Highline Vail - a DoubleTree by Hilton

4 out of 5
West Vail
Price was CA $2,654, price is now CA $1,851 per person
CA $1,851
per person
Mar 28 - Apr 4
found 9 hours ago
Roundtrip flight included
Toronto (YYZ) to Denver (DEN)
8.6/10 Excellent! (805 reviews)
The staff were very courteous!

Reviewed on Jan 2, 2026

Tivoli Lodge

Tivoli Lodge

4 out of 5
Vail Village
Price was CA $3,574, price is now CA $2,250 per person
CA $2,250
per person
Mar 28 - Apr 4
found 9 hours ago
Roundtrip flight included
Toronto (YYZ) to Denver (DEN)
9.4/10 Exceptional! (1,003 reviews)
Great location Staff was very nice.

Reviewed on Feb 11, 2026

Manor Vail Lodge

Manor Vail Lodge

4.5 out of 5
Vail Village
Price was CA $4,786, price is now CA $3,202 per person
CA $3,202
per person
Mar 28 - Apr 4
found 9 hours ago
Roundtrip flight included
Toronto (YYZ) to Denver (DEN)
9.6/10 Exceptional! (714 reviews)
Room was spacious and very accommodating. Staff was great. Breakfasts were excellent. Close to mountain.

Reviewed on Feb 11, 2026

The Ritz-Carlton Residences, Vail

The Ritz-Carlton Residences, Vail

4.5 out of 5
Lionshead
Price was CA $16,237, price is now CA $11,603 per person
CA $11,603
per person
Mar 28 - Apr 4
found 9 hours ago
Roundtrip flight included
Toronto (YYZ) to Denver (DEN)
9.6/10 Exceptional! (162 reviews)
Our stay here exceeded our expectations! Amazing staff! Amazing place! 10/10 recommend

Reviewed on Dec 7, 2025

Elkhorn Lodge

Elkhorn Lodge

4.5 out of 5
Beaver Creek
Price was CA $5,499, price is now CA $4,036 per person
CA $4,036
per person
Mar 28 - Apr 4
found 9 hours ago
Roundtrip flight included
Toronto (YYZ) to Denver (DEN)
9.8/10 Exceptional! (80 reviews)
Great facilities. Helpful staff. Nice unit - well appointed!

Reviewed on Dec 8, 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
Summer time in Boulder, CO - Chautauqua Mountain

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

Hotel Boulderado

Hotel Boulderado

4 out of 5
2115 13th St Boulder CO
Fully refundableReserve now, pay when you stay
9.4/10 Exceptional! (1,648 reviews)
Very clean. Nice staff.

Reviewed on Feb 11, 2026

Get rates
Hotel Boulderado
Days Inn by Wyndham Thornton

Days Inn by Wyndham Thornton

2.5 out of 5
12101 N. Grant St. Thornton CO
Fully refundableReserve now, pay when you stay
The price is CA $80 per night from Feb 17 to Feb 18
CA $80
CA $89 total
Feb 17 - Feb 18
includes taxes & fees
7.4/10 Good! (592 reviews)
Clean room

Reviewed on Feb 11, 2026

Days Inn by Wyndham Thornton
Omni Interlocken

Omni Interlocken

4 out of 5
500 Interlocken Blvd Broomfield CO
Fully refundableReserve now, pay when you stay
The price is CA $228 per night from Mar 1 to Mar 2
CA $228
CA $287 total
Mar 1 - Mar 2
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
Clean quiet spacious room with comfortable bed

Reviewed on Feb 10, 2026

Omni Interlocken
See all 1,820 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
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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 $1,851. 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 featuring a fountain

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