Timber Trail Vacation Packages

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Top Holiday Package Deals in Timber Trail

Price found within the past 48 hours. Click for updated prices.
Laurelwood Condominiums

Laurelwood Condominiums

3 out of 5
Price was CA $2,603, price is now CA $2,035 per person
CA $2,035
per person
Jan 16 - Jan 20
found 5 hours ago
Roundtrip flight included
Toronto (YTO) to Denver (DEN)
9.2/10 Wonderful! (1,577 reviews)
Great place to stay. Very clean and well represented.

Reviewed on Nov 8, 2026

Residences at the Little Nell

Residences at the Little Nell

5 out of 5
Downtown Aspen
Price was CA $7,294, price is now CA $5,468 per person
CA $5,468
per person
Jan 16 - Jan 20
found 5 hours ago
Roundtrip flight included
Toronto (YTO) to Denver (DEN)
9.8/10 Exceptional! (185 reviews)

Aspen Hideaway by Avantstay Walk to Aspen, Near Slopes + Pool & Hot Tub Access

Aspen Hideaway by Avantstay Walk to Aspen, Near Slopes + Pool & Hot Tub Access

3 out of 5
West End
Price was CA $3,516, price is now CA $2,701 per person
CA $2,701
per person
Jan 16 - Jan 20
found 5 hours ago
Roundtrip flight included
Toronto (YTO) to Denver (DEN)
No reviews

Hotel Jerome, Auberge Collection

Hotel Jerome, Auberge Collection

5 out of 5
Downtown Aspen
Price was CA $9,469, price is now CA $7,487 per person
CA $7,487
per person
Jan 16 - Jan 20
found 5 hours ago
Roundtrip flight included
Toronto (YTO) to Denver (DEN)
9.6/10 Exceptional! (487 reviews)

Stonebridge Inn

Stonebridge Inn

4 out of 5
Price was CA $2,748, price is now CA $2,176 per person
CA $2,176
per person
Jan 16 - Jan 20
found 5 hours ago
Roundtrip flight included
Toronto (YTO) to Denver (DEN)
8.2/10 Very good! (1,000 reviews)
THE place to be at Snowmass!! Do not hesitate and stay here instead of Aspen if goong for a skiing adventire. Grat locarion, superb dinning at the restaurant a nd within walking distance to the mall

Reviewed on Jul 14, 2026

Where to stay in Timber Trail

Find the best Timber Trail areas and neighborhoods for the activities you enjoy most. Learn more about Timber Trail
A street with a green-roofed building, parked cars, and outdoor seating with yellow umbrellas.

Historic District

4 out of top 10 points of interest in this area

The picture-perfect mountain views and popular ski slopes are top of the list for many visitors to Historic District. A stop by Breckenridge Ski Resort or Quandary Antiques Cabin & Ceramic Studio might round out your trip.

Find hotels in Historic District

Timber Trail Hotel Deals

Timber Trail Lodge: One Ski Hill Access w/ Private Shuttle, Hot Tub, Sauna

Timber Trail Lodge: One Ski Hill Access w/ Private Shuttle, Hot Tub, Sauna

Breckenridge CO
10/10 Exceptional! (107 reviews)
Beautiful vacation property
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: we loved this property and we had a great stay ..."

Reviewed on Oct 11, 2026

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Timber Trail Lodge: One Ski Hill Access w/ Private Shuttle, Hot Tub, Sauna
Keystone Lodge & Spa, A Vail Resorts Property

Keystone Lodge & Spa, A Vail Resorts Property

4 out of 5
22101 US Highway 6 Keystone CO
Fully refundableReserve now, pay when you stay
The price is CA $199 per night from Nov 13 to Nov 14
CA $199
CA $262 total
Nov 13 - Nov 14
includes taxes & fees
Keystone Lodge & Spa, A Vail Resorts Property
Village at Breckenridge, A Vail Resorts Property

Village at Breckenridge, A Vail Resorts Property

3 out of 5
535 S Park Avenue Breckenridge CO
Fully refundableReserve now, pay when you stay
The price is CA $207 per night from Nov 23 to Nov 24
CA $207
CA $260 total
Nov 23 - Nov 24
includes taxes & fees
8.4/10 Very good! (2,180 reviews)
"So close to the town, could walk to dinner. Loved the location."

Reviewed on Nov 9, 2026

Village at Breckenridge, A Vail Resorts Property
See all 12,913 properties in Timber 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.
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Frequently asked questions

How much does a Timber Trail vacation package cost?
Our Timber Trail vacation packages, which begin from just CA $2,035, are an ideal way to save big bucks. Select your favorite hotels, flights and rental car to create your dream getaway.
How do I get a cheap travel package to Timber Trail?
You'll save tons of cash if you combine your hotels, car rentals and flights into a Timber Trail vacation package. Sometimes cheap means fewer choices. But that's not the case with Expedia. We offer over 550 air carriers and 1,000,000 properties across the globe, which means you'll always have plenty of variety to choose from. Like to save even more? Add some exciting activities to your package deal and unlock even more bargains! After all, travel is about more than simply getting to your destination.
Where should I stay in Timber Trail?
Stay close to the action. Many people like to book hotels in the vicinity of popular sights, such as Breckenridge Ski Resort, Beaver Run SuperChair and Breckenridge Riverwalk Center.
What are the top hotels in Timber Trail?
Ski Hi Lodge: Hot Tub, True Ski and Slopeside Manor 6 Bedroom Home are two of the most popular properties in Timber Trail. Why not look up the facilities and rates at each and then make up your mind?
How far in advance should I book my Timber Trail vacation?
While not all air carriers release tickets early, you can normally start comparing international airfares on Expedia up to a year in advance. This is when you'll score some fantastic deals. If you've left everything to the last minute, you might still be in luck. Sometimes the cheapest prices emerge just weeks prior to departure.
What does an Expedia Timber Trail travel package include?
Flights, rental cars and hotels, or any combination of them — the choice is all yours! Whether you're venturing to Timber Trail with the whole family or traveling solo, there's a package to fit every style and budget. Once you've made your booking, why not add on a few tours as well?
What should I know before booking a Timber Trail travel package?
So many places to wander around, so many things to do. With a package, you'll be able to cross more of them off your list. Bundle your hotels, flights and rental cars and see how much you save.
Can I choose my airline with a Timber Trail Expedia vacation package?
Most definitely. We offer more than 550 airlines around the world, so you can customize your Timber Trail getaway according to your travel preferences.
If I'm not able to travel, can I cancel my Timber Trail vacation package?
Your situation can change without warning, so yes, you can. You may be able to cancel and rebook your Timber Trail vacation package at no cost if you've booked in the last 24 hours. For bookings made more than 24 hours ago, you can still make the necessary changes, but your car rental company, airline or hotel may charge a fee. Looking for more information? Check out our Customer Service Portal. We'll help make sure your getaway goes off without a hitch.

Things to do

Breckenridge Dark Sky Star Tour

Breckenridge Dark Sky Star Tour

CA $87
per adult
Breckenridge Dark Sky Star Tour
Fat Tire E Bike Rental in Breckenridge Delivered to you

Fat Tire E Bike Rental in Breckenridge

CA $120
per adult
Fat Tire E Bike Rental in Breckenridge
Breckenridge Dark Sky Star Tour

Breckenridge Dark Sky Star Tour

CA $87
per adult
Breckenridge Dark Sky Star Tour
See all activities in Breckenridge
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.