The Highlands Vacation Packages

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Top Holiday Package Deals in The Highlands

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Hotel & Suites Denver Airport by IHG

Holiday Inn Express Hotel & Suites Denver Airport by IHG

2.5 out of 5
per person
Sep 25 - Oct 2
found 10 hours ago
Roundtrip flight included
Toronto (YTO) to Denver (DEN)
9/10 Wonderful! (1,010 reviews)
Parking was horrible, could have been cleaner

Reviewed on Jul. 26, 2025

The Crawford Hotel

The Crawford Hotel

5 out of 5
LoDo
per person
Sep 25 - Oct 2
found 10 hours ago
Roundtrip flight included
Toronto (YTO) to Denver (DEN)
9.2/10 Wonderful! (1,001 reviews)
I loved how charming it was. What a beautiful hotel in a train station. I liked how it had its own separate entrance from the public. The bars and coffee shops inside give you one free drink a day or a discount. That was a perk that I also enjoyed. Plus Its really a great location. Central to all of Denver and its fun!

Reviewed on Jul. 25, 2025

The Slate Denver, Tapestry Collection By Hilton

The Slate Denver, Tapestry Collection By Hilton

4 out of 5
Downtown Denver
per person
Sep 25 - Oct 2
found 10 hours ago
Roundtrip flight included
Toronto (YTO) to Denver (DEN)
9.4/10 Exceptional! (1,310 reviews)
The fact that this is in an old school building and they integrated that into the design is remarkable.

Reviewed on Jul. 25, 2025

Hotel Indigo Denver Downtown - Union Station by IHG

Hotel Indigo Denver Downtown - Union Station by IHG

3.5 out of 5
LoDo
per person
Sep 25 - Oct 2
found 10 hours ago
Roundtrip flight included
Toronto (YTO) to Denver (DEN)
9/10 Wonderful! (1,018 reviews)
Great property with great location. It’s very close to the baseball stadium and the restaurants and bars around it. The property was clean and the room view was great. Only complaint was we didn’t get our room until after check-in time.

Reviewed on Jul. 25, 2025

Kimpton Hotel Monaco Denver by IHG

Kimpton Hotel Monaco Denver by IHG

4 out of 5
Downtown Denver
per person
Sep 25 - Oct 2
found 10 hours ago
Roundtrip flight included
Toronto (YTO) to Denver (DEN)
8.6/10 Excellent! (1,006 reviews)
The property was in a convenient location. It's an older hotel, but has been updated nicely. The parking was expensive at this location, but alternate parking was close by. There were many dining/entertainment options at a walkable distance.

Reviewed on Jul. 21, 2025

Where to stay in The Highlands

Find the best The Highlands areas and neighborhoods for the activities you enjoy most. Learn more about The Highlands
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 Main Street might round out your trip.

Find hotels in Historic District

The Highlands Hotel Deals

Hyatt Vacation Club at The Ranahan

Hyatt Vacation Club at The Ranahan

4 out of 5
557 Stan Miller Dr, Breckenridge, CO
The price is CA $185 per night from Aug 25 to Aug 26
CA $185
CA $262 total
Aug 25 - Aug 26
includes taxes & fees
9.4/10 Exceptional! (1,426 reviews)
"Amazing"

Reviewed on Jul. 25, 2025

Hyatt Vacation Club at The Ranahan
Pine Crest Lodge: Custom Log Home, Private Hot Tub, Bocce, Fire Pit

Pine Crest Lodge: Custom Log Home, Private Hot Tub, Bocce, Fire Pit

Breckenridge
9.8/10 Exceptional! (53 reviews)
Work Retreat
"Great spot for a work retreat. Great places to gather plus plenty of room to spread out. Kitchen amenities were top notch. Having some spices and seasonings in the cupboard was a plus. Wine fridge and ice maker were also great."

Reviewed on Jun. 25, 2025

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Pine Crest Lodge: Custom Log Home, Private Hot Tub, Bocce, Fire Pit
Amazing Mountain Views, Sleeps 16, Hot Tub, Sauna, Guest House, Golf Course

Amazing Mountain Views, Sleeps 16, Hot Tub, Sauna, Guest House, Golf Course

BRECKENRIDGE
9.6/10 Exceptional! (68 reviews)
Great stay!!
"We had a wonderful time at this cabin in Breckenridge. We even saw a moose off of our back deck! Highly recommend this property!"

Reviewed on Sep. 6, 2024

Get rates
Amazing Mountain Views, Sleeps 16, Hot Tub, Sauna, Guest House, Golf Course
See all 12,738 properties in The Highlands
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 The Highlands vacation package cost?
Starting from as low as CA $1,116, a package is your portal to cheaper travel. Custom make your The Highlands adventure by selecting from our wide range of airfares, hotels and rental cars.
How do I get a cheap travel package to The Highlands?
One of the simplest ways to save cash (and time) is to combine your bookings with Expedia. Flights, hotels, activities and rental cars — we've got everything you need. Select the combination that best suits you and see your savings stack up. We know a travel package is never one-size-fits-all. That's why we offer more than 550 partner airlines and 1,000,000 properties throughout the world, which lets you customize your The Highlands getaway.
Where should I stay in The Highlands?
With lots to explore in The Highlands, we suggest you lock in a hotel near its attractions. Breckenridge Riverwalk Center, BreckConnect Gondola and Breckenridge Golf Club are some good ones to add to your to-do list.
What are the top hotels in The Highlands?
If it's your first time in The Highlands, lock in a room at Remodeled 2 Level Condo With A Fireplace or Tasteful Mountain Abode: 3 Mi To Breckenridge. Both hotels offer comfortable beds and are popular options with many travelers.
How far in advance should I book my The Highlands vacation?
It depends on the air carrier, but you can usually browse through international flights on Expedia up to a year in advance. While it's generally recommended to book ahead of time, lucky travelers occasionally score a cheaper flight only weeks before their intended journey.
What does an Expedia The Highlands travel package include?
From hotels and airfares to rental cars, Expedia can help you shape a The Highlands package that fits you. Heading off for a few weeks? Consider a hotel, rental car and flight bundle. If you're taking a quick break, a hotel and airfare deal may suit you better. Experiences can also be added once you've made your booking. Our vacation packages make it easy to plan and save.
What should I know before booking a The Highlands travel package?
A package can be more affordable than individually booking all you need for your trip. For example, bundle your hotels, flights and rental cars and score big savings. Whatever your vacation plans, you'll find a package to suit your budget.
Can I choose my airline with a The Highlands Expedia vacation package?
Most definitely. Expedia has over 550 partner airlines to select from globally. With so many choices, finding the right carrier to bring you to The Highlands will be a snap.
If I'm not able to travel, can I cancel my The Highlands vacation package?
You sure can, and we'll help you every step of the way. You may be able to cancel or change your The Highlands vacation package for free if you booked in the last 24 hours. But you may incur a fee from your airline, hotel or car rental company for older bookings. If your circumstances unexpectedly change, browse our Customer Service Portal for further information.

Discover the most popular places to visit in The Highlands

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.