Winterwood Vacation Packages

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Top Holiday Package Deals in Winterwood

Price found within the past 48 hours. Click for updated prices.
Hyatt Vacation Club at The Ranahan

Hyatt Vacation Club at The Ranahan

4 out of 5
Northside Breck
Price was CA $1,261, price is now CA $791 per person
CA $791
per person
Oct 12 - Oct 18
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Denver (DEN)
9.6/10 Exceptional! (1,453 reviews)
Modern lodge with an excellent staff. Easy parking. Well furnished and spacious rooms. Excellent fitness center. Main Street Breckenridge is around 3 miles drive or shuttle ride from hotel. Great place to stay.

Reviewed on Aug. 23, 2025

The Brown Palace Hotel and Spa, Autograph Collection

The Brown Palace Hotel and Spa, Autograph Collection

4.5 out of 5
Downtown Denver
Price was CA $2,744, price is now CA $1,757 per person
CA $1,757
per person
Oct 6 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Denver (DEN)
8.6/10 Excellent! (1,000 reviews)
Hotel was beautiful but the room was rough. The bathroom sinks when turned on leaked from the handles bad. The shower head was pretty much siliconed on. The toilet paper holder was hanging on by a thread. Had to call and go down to request coffee and water several times. After 3 days someone showed up to give us coffee and water. Cleaned the room once. Wont ever stay again. Our rental car was in valet and there was an accident.

Reviewed on Aug. 18, 2025

The Ritz-Carlton Residences, Vail

The Ritz-Carlton Residences, Vail

4.5 out of 5
Lionshead
Price was CA $3,925, price is now CA $2,586 per person
CA $2,586
per person
Sep 26 - Oct 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Denver (DEN)
9.6/10 Exceptional! (156 reviews)
Amazing Staff! Thank you Anna!

Reviewed on Jul. 15, 2025

The Crawford Hotel

The Crawford Hotel

5 out of 5
LoDo
Price was CA $1,923, price is now CA $1,282 per person
CA $1,282
per person
Nov 7 - Nov 12
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Denver (DEN)
9.4/10 Exceptional! (1,003 reviews)
Beautiful decor, outstanding service, great restaurant, and location!

Reviewed on Aug. 21, 2025

The Residences at Main Street Station, Breckenridge

The Residences at Main Street Station, Breckenridge

4 out of 5
Historic District
Price was CA $1,845, price is now CA $1,254 per person
CA $1,254
per person
Sep 26 - Oct 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Denver (DEN)
8.8/10 Excellent! (132 reviews)
First time staying here. Didn’t stay long enough to actually give a good review.

Reviewed on Aug. 6, 2025

Where to stay in Winterwood

Find the best Winterwood areas and neighborhoods for the activities you enjoy most. Learn more about Winterwood
Breckenridge featuring street performance, snow and outdoor art

Historic District

3 out of top 10 points of interest in this area
4/5(1 area review)

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 Breckenridge Arts District might round out your trip.

Find hotels in Historic District

Winterwood Hotel Deals

Beaver Run Resort & Conference Center

Beaver Run Resort & Conference Center

3.5 out of 5
620 Village Rd, Breckenridge, CO
The price is CA $230 per night from Sep 1 to Sep 2
CA $230
CA $274 total
Sep 1 - Sep 2
includes taxes & fees
8.2/10 Very Good! (1,000 reviews)
"Staff and facilities good. Parking is limited."

Reviewed on Aug. 20, 2025

Beaver Run Resort & Conference Center
Hyatt Vacation Club at The Ranahan

Hyatt Vacation Club at The Ranahan

4 out of 5
557 Stan Miller Dr, Breckenridge, CO
Fully refundable
The price is CA $198 per night from Sep 23 to Sep 24
CA $198
CA $277 total
Sep 23 - Sep 24
includes taxes & fees
9.4/10 Exceptional! (1,457 reviews)
"The property was was very clean, well maintained and amenities well thought out. Location is a few miles from town, but quick easy drive or a shuttle that runs every 30 minutes till 9pm. Great patios/decks with nice outdoor furniture."

Reviewed on Aug. 22, 2025

Hyatt Vacation Club at The Ranahan
The Lodge at Breckenridge

The Lodge at Breckenridge

3.5 out of 5
112 Overlook Drive, Breckenridge, CO
Fully refundableReserve now, pay when you stay
The price is CA $183 per night from Sep 7 to Sep 8
CA $183
CA $242 total
Sep 7 - Sep 8
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
Amazing Stay
"It was an incredible stay! We were so pleasantly surprised by its rustic x modern look. It was clean and accommodated all our needs: hot tubs, fire pits, corn hole, a restaurant, a bar, readily accessible water and ice… and the views were INCREDIBLE!! highly recommend booking a mountain view room. ..."

Reviewed on Aug. 19, 2025

The Lodge at Breckenridge
See all 12,870 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.
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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 $791. 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.

Discover the most popular places to visit in Winterwood

Breckenridge Ski Resort featuring snow skiing, forests and snow

Breckenridge Ski Resort

A ski resort that impresses visitors with five breathtaking peaks, a huge variety of slopes and fantastic modern facilities. Nearby is a charming Victorian-era town.

Breckenridge Ski Resort
Breckenridge featuring street performance, snow and outdoor art

Main Street

During your visit to Breckenridge, you can browse for the perfect souvenirs at Main Street. Discover the area's mountain views and seek out the ski slopes.

Main Street

Beaver Run SuperChair

Enjoy a trip to Beaver Run SuperChair and popular activities like skiing in Breckenridge. Wander the lakeside or discover the area's mountain views.

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