The Highlands Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest The Highlands Vacation Packages
- Laurelwood Condominiums
Jan 16 - Jan 20Laurelwood Condominiums + Flight
Snowmass Village4 nights3.0 star property9.2/10 - Wonderful (1,589 reviews)"Great place to stay. Very clean and well represented."Reviewed November 8, 2026Roundtrip • Toronto (YTO) - Denver (DEN)YYZ - DEN • Nonstop DEN - YHM • 1 stopCA $2,604CA $2,035found 10 hours agoper traveller - Residences at the Little Nell
Jan 16 - Jan 20Residences at the Little Nell + Flight
Downtown Aspen4 nights5.0 star property9.8/10 - Exceptional (186 reviews)Roundtrip • Toronto (YTO) - Denver (DEN)YYZ - DEN • Nonstop DEN - YHM • 1 stopCA $7,294CA $5,469found 10 hours agoper traveller - Aspen Hideaway by Avantstay Walk to Aspen, Near Slopes + Pool & Hot Tub Access
Jan 16 - Jan 20Aspen Hideaway by Avantstay Walk to Aspen, Near Slopes + Pool & Hot Tub Access + Flight
West End4 nights3.0 star propertyRoundtrip • Toronto (YTO) - Denver (DEN)YYZ - DEN • Nonstop DEN - YHM • 1 stopCA $3,517CA $2,701found 10 hours agoper traveller - Hotel Jerome, Auberge Collection
Jan 16 - Jan 20Hotel Jerome, Auberge Collection + Flight
Downtown Aspen4 nights5.0 star property9.6/10 - Exceptional (488 reviews)Roundtrip • Toronto (YTO) - Denver (DEN)YYZ - DEN • Nonstop DEN - YHM • 1 stopCA $9,469CA $7,488found 10 hours agoper traveller - Stonebridge Inn
Jan 16 - Jan 20Stonebridge Inn + Flight
Snowmass Village4 nights4.0 star property8.2/10 - 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 July 14, 2026Roundtrip • Toronto (YTO) - Denver (DEN)YYZ - DEN • Nonstop DEN - YHM • 1 stopCA $2,748CA $2,177found 10 hours agoper traveller
Where to stay in The Highlands
Historic District
Peak 9
Peak 8
Four O'Clock
Peak 7
The Highlands Hotel Deals
"Great location! Hot tub and fire pits amazing!"
The Residences at Main Street Station, Breckenridge
The Residences at Main Street Station, Breckenridge
Gravity Haus Breckenridge
Gravity Haus Breckenridge
The Lodge at Breckenridge
The Lodge at Breckenridge
Lakefront Breckenridge Cabin: 6 Mi to Ski Resort!
Lakefront Breckenridge Cabin: 6 Mi to Ski Resort!"Smaller than picture. Very clean and the hosts were great. I would not recommend more than 2 people to stay."
River Mountain Lodge, A Vail Resorts Property
River Mountain Lodge, A Vail Resorts Property"Great place to stay definitely will come back"
Residence Inn by Marriott Breckenridge
Residence Inn by Marriott Breckenridge"Great staff especially Athena and the lady in the bar they are very accommodating. Great customer service."
Frequently Asked Questions
How much does a The Highlands vacation package cost?
Starting from as low as CA $2,035, 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.