Winterwood Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Winterwood

Price found within the past 48 hours. Click for updated prices.
The Source Hotel

The Source Hotel

4.5 out of 5
River North Art District
Price was CA $1,443, price is now CA $1,241 per person
CA $1,241
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Denver (DEN)
8.8/10 Excellent! (1,004 reviews)
Industrial style hotel in an industrial area. Good stay, little difficult walk from 38th & Blake station with a suitcase. HVAC system didn’t work well and no coffee available until 10:00 am, these are my only complaints. Empty food hall attached but restaurants that were open were great. Included free drink at rooftop bar was a plus and nice pool & hot tub. Good value for the price

Reviewed on Nov 9, 2026

Laurelwood Condominiums

Laurelwood Condominiums

3 out of 5
Price was CA $3,176, price is now CA $2,339 per person
CA $2,339
per person
Feb 3 - Feb 7
found 1 day 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

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
Save 100% on your flight
Price was CA $5,804, price is now CA $4,342 per person
CA $4,342
per person
Jan 27 - Feb 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Denver (DEN)
No reviews

Terracehouse - CoralTree Residence Collection

Terracehouse - CoralTree Residence Collection

3 out of 5
Price was CA $5,034, price is now CA $3,983 per person
CA $3,983
per person
Feb 3 - Feb 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Denver (DEN)
9/10 Wonderful! (69 reviews)
Beautiful, spacious condo conveniently located next to the shops and restaurants of Snowmass Village, offering plenty of outdoor community amenities, including a large firepit area, a secluded hammock for relaxing, and a gorgeous hot tub. We will definitely stay at this property again.

Reviewed on Aug 10, 2025

HOLT - Billionaire Mountain

HOLT - Billionaire Mountain

3.5 out of 5
Downtown Aspen
Price was CA $3,306, price is now CA $2,672 per person
CA $2,672
per person
Feb 3 - Feb 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Denver (DEN)
8.4/10 Very good! (16 reviews)

Where to stay in Winterwood

Find the best Winterwood areas and neighborhoods for the activities you enjoy most. Learn more about Winterwood
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

Winterwood Hotel Deals

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
8.8/10 Excellent! (1,063 reviews)
"A bit dated but nice location. Has all the amenities you could want. They charge to park"

Reviewed on Nov 8, 2026

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! (2,179 reviews)
"Beautiful room, location was great to walk around town and get some fresh air."

Reviewed on Nov 5, 2026

Village at Breckenridge, A Vail Resorts Property
Hyatt Vacation Club at The Ranahan

Hyatt Vacation Club at The Ranahan

4 out of 5
557 Stan Miller Dr Breckenridge CO
Fully refundableReserve now, pay when you stay
The price is CA $136 per night from Nov 17 to Nov 18
CA $136
CA $209 total
Nov 17 - Nov 18
includes taxes & fees
Hyatt Vacation Club at The Ranahan
See all 13,196 properties in Winterwood
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 Winterwood vacation package cost?
Choose from any combination of car rentals, flights and hotels, and you can be vacationing in Winterwood from just CA $1,241. And the more you bundle, the more money you save. The getaway of your dreams has never been more affordable.
How do I get a cheap travel package to Winterwood?
One of the simplest ways to save dollars (and time) is to combine your bookings with Expedia. Flights, hotels, rental cars and activities — we've got them all covered. Choose a combination that suits your style and see your savings pile up. Of course, a travel package is never a one-size-fits-all. That's why we offer over 550 partner airlines and 1,000,000 hotel options from all over the world, which lets you customize your Winterwood vacation.
Where should I stay in Winterwood?
A vacation in Winterwood isn't complete without checking out Breckenridge Ski Resort, Beaver Run SuperChair and Breckenridge Riverwalk Center. Stay close to these tourist attractions and make sightseeing a breeze.
What are the top hotels in Winterwood?
Reserve a room at The Flurry Lodge - Four Bedroom House. It's one of this area's most in-demand properties. Another reputable option in Winterwood is Peak 7 Breckenridge Retreat, 4 Br.
How far in advance should I book my Winterwood vacation?
While not all air carriers release tickets early, customers are usually able to look up international fares on Expedia up to a year in advance. This is when you can score some incredible deals. If you're purchasing tickets last minute, you might still get lucky. Low prices sometimes become available a few weeks prior to departure.
What does an Expedia Winterwood travel package include?
Much of that depends on you. You can select from a variety of Winterwood packages, such as a hotel, rental car and flight. You can also book a hotel with a flight, or a flight with a rental car. Once you've made your booking, you can add on the fun stuff like activities and tours. Whatever your perfect Winterwood vacation looks like, you'll save!
What should I know before booking a Winterwood travel package?
Bundling your bookings into a Winterwood vacation package is the easiest way to organize your trip. Not only that, you'll save just for combining your hotels, flights and car rentals. Once you've booked, why not add on a day tour or an activity?
Can I choose my airline with a Winterwood Expedia vacation package?
Yes — that's the beauty of an Expedia package. You get to decide. We have access to more than 550 partner airlines worldwide, so you have loads of choice when organizing your Winterwood adventure.
If I'm not able to travel, can I cancel my Winterwood vacation package?
If your vacation plans in Winterwood have changed, it's comforting to know that it's possible to cancel or amend your booking. If you booked less than 24 hours ago, you may be able to receive a refund. If your booking is older than that, your hotel, airline or car rental company may impose fees. To learn more, check our Customer Service Portal.

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.