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.
Tivoli Lodge
Vail Village
CA $1,415
per person
Dec 8 - Dec 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Denver (DEN)
9.2/10 Wonderful! (1,206 reviews)
Nice hotel, cozy rooms, mountain lodge decor, fantastic employees and customer service. Hot tub is amazing, beds are super plush and comfortable.
Reviewed on Sep 20, 2026
Beaver Run Resort & Conference Center
Peak 9
CA $1,452
per person
Dec 8 - Dec 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Denver (DEN)
8.4/10 Very good! (1,287 reviews)
This was such a great hotel for our family. The kids had fun at the arcade. The pools were the perfect temperature. Hot tubs were great. We had such a relaxing time. My only critique would be that I wish the bar across from the arcade was open and our room didn’t have AC.
Reviewed on Sep 14, 2026
Flying Horse Resort & Club
Flying Horse
CA $1,379
per person
Dec 8 - Dec 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Denver (DEN)
9.4/10 Exceptional! (925 reviews)
This was my 4th or 5th stay at Flying Horse. I love it. Room is big, views are really good and staff is excellent. Couple that with the outstanding steakhouse that’s right there and I’ll keep coming back.
Reviewed on Sep 14, 2026
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
Historic District
3 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 Main Street might round out your trip.
Peak 9
3 out of top 10 points of interest in this area
The captivating mountain views and stunning ski slopes are top of the list for many visitors to Peak 9. A stop by Breckenridge Ski Resort or Peak 8 SuperConnect Lift might round out your trip.
Peak 8
Unique features of Peak 8 include the skiing and mountain views. Make a stop by Breckenridge Ski Resort or Four O'Clock Ski Run while you're exploring the area.
Four O'Clock
1 out of top 10 points of interest in this area
The captivating mountain views and stunning ski slopes are top of the list for many visitors to Four O'Clock. A stop by Breckenridge Ski Resort or Snowflake Chair Lift might round out your trip.
Peak 7
1 out of top 10 points of interest in this area
While visiting Peak 7, you might make a stop by sights like Breckenridge Ski Resort and Breckenridge Nordic Center.
The Highlands Hotel Deals
Hyatt Vacation Club at The Ranahan
557 Stan Miller Dr Breckenridge CO
CA $139
CA $211 total
Oct 20 - Oct 21
includes taxes & fees
Pine Crest Lodge: Custom Log Home, Private Hot Tub, Bocce, Fire Pit
Breckenridge CO
Keystone Lodge & Spa, A Vail Resorts Property
22101 US Highway 6 Keystone CO
Fully refundableReserve now, pay when you stay
CA $161
CA $212 total
Oct 3 - Oct 4
includes taxes & fees
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.
Frequently asked questions
How much does a The Highlands vacation package cost?
Starting from as low as CA $1,254, 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.
Stay near popular The Highlands attractions
Breckenridge Golf Club
8.8/10 (18 reviews)
Play a round of golf in Breckenridge at Breckenridge Golf Club, and enjoy other activities such as skiing. Wander the lakeside or discover the area's mountain views.
Things to do
Breckenridge Tours - Strange but True
CA $46
per adult
80% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.