Overland 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

The Latest Overland Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Feb 3 - Feb 7

    Wedgewood Lodge + Flight

    Peak 8
    4 nights
    3.5 star property
    9.4/10 - Exceptional (473 reviews)
    Roundtrip • Toronto (YTO) - Denver (DEN)
    YYZ - DEN • Nonstop DEN - YYZ • 1 stop
    CA $2,280
    CA $1,782
    per traveller
    found 1 day ago
    Wedgewood Lodge
  • Jan 16 - Jan 20

    Residences at the Little Nell + Flight

    Downtown Aspen
    4 nights
    5.0 star property
    9.8/10 - Exceptional (186 reviews)
    Roundtrip • Toronto (YTO) - Denver (DEN)
    YYZ - DEN • Nonstop DEN - YHM • 1 stop
    CA $7,294
    CA $5,469
    per traveller
    found 1 day ago
    Residences at the Little Nell
  • Jan 16 - Jan 20

    Aspen Hideaway by Avantstay Walk to Aspen, Near Slopes + Pool & Hot Tub Access + Flight

    West End
    4 nights
    3.0 star property
    Roundtrip • Toronto (YTO) - Denver (DEN)
    YYZ - DEN • Nonstop DEN - YHM • 1 stop
    CA $3,517
    CA $2,701
    per traveller
    found 1 day ago
    Aspen Hideaway by Avantstay Walk to Aspen, Near Slopes + Pool & Hot Tub Access
  • Jan 16 - Jan 20

    Laurelwood Condominiums + Flight

    Snowmass Village
    4 nights
    3.0 star property
    9.2/10 - Wonderful (1,590 reviews)
    Roundtrip • Toronto (YTO) - Denver (DEN)
    YYZ - DEN • Nonstop DEN - YHM • 1 stop
    CA $2,604
    CA $2,035
    per traveller
    found 1 day ago
    Laurelwood Condominiums
  • Jan 16 - Jan 20

    Hotel Jerome, Auberge Collection + Flight

    Downtown Aspen
    4 nights
    5.0 star property
    9.6/10 - Exceptional (488 reviews)
    Roundtrip • Toronto (YTO) - Denver (DEN)
    YYZ - DEN • Nonstop DEN - YHM • 1 stop
    CA $9,469
    CA $7,488
    per traveller
    found 1 day ago
    Hotel Jerome, Auberge Collection

Where to stay in Overland

Find the best Overland areas and neighborhoods for the activities you enjoy most.

Downtown Denver

Dive into this bustling financial and entertainment hub, featuring the 16th Street pedestrian mall, Larimer Square, and the Theatre District. Catch a game at Coors Field or Ball Arena, and explore the neighborhood's vibrant dining scene.

Cherry Creek

Experience a blend of urban and residential vibes in Denver's Cherry Creek, where tree-lined streets meet shopping and dining at Cherry Creek North. Explore Fillmore Plaza, Manley and Pulaski Parks, or hop on the easily accessible public bus system.

Denver Tech Center

Known for its ample dining options and great live music, there's plenty to explore in Denver Tech Center. You can visit top attractions like Fiddler's Green Amphitheatre and The Landmark Theatre Greenwood Village, and jump on the metro at Orchard Station or Arapahoe at Village Center Station to see more of the city.

LoDo

Historic district with vibrant nightlife, LoDo offers a mix of clubs, art galleries, boutiques, and over 70 bars and restaurants. Must-visit spots include Coors Field, Ball Arena, and Denver Union Station. Enjoy its walkable, pedestrian-friendly streets.

Highlands Ranch

Highlands Ranch is popular for its abundant dining options, and if you're looking for more to see and do, you might think about a trip to South Suburban Sports Complex or Chatfield State Park.

Discover the most popular places to visit in Overland

What to do near Overland

Overland Hotel Deals

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 an Overland vacation package cost?

Handcraft your Overland vacation package from just CA $1,782. Choose from any combination of hotels, flights and rental cars to create the trip you've been dreaming of. Remember to add on some tours and experiences!

How do I get a cheap travel package to Overland?

Combining your hotel and flight with Expedia won't just save valuable time — it'll save you a nice amount too. An Overland vacation package makes it a cinch to organize your perfect trip. With more than 550 airlines all over the world to choose from, finding convenient flights that fit your busy schedule won't be a challenge. On top of that, we have over 1,000,000 properties globally to pick from. Now that's choice! No matter who you are, Expedia puts more of the world within your reach.

Where should I stay in Overland?

A getaway to Overland wouldn't be complete without paying a visit to University of Denver, Washington Park and Magness Arena. Stay near these popular attractions and make sightseeing a breeze.

What are the top hotels in Overland?

Whether you aim to stay for a night or a week in Overland, you'll get a wonderful night's rest at Roof Top Patio, Hot Tub, And Minutes From Downtown. This place is a top choice for lots of travelers.

How far in advance should I book my Overland vacation?

It's difficult to pick the best time for airfares, but we generally say the earlier, the better. Many international flights on Expedia become available up to 12 months in advance. If you're booking last minute, fear not. Cheap prices occasionally appear just weeks before departure dates.

What does an Expedia Overland travel package include?

Flights, rental cars and hotels — we have them well covered. With Expedia, you can create your Overland travel package your way. All you have to do is figure out exactly what you need. Once you've made your booking, you can add on fun things like experiences and activities. The more you bundle, the greater your savings!

What should I know before booking an Overland travel package?

You can look forward to saving with an Expedia travel package. Combine your flights, rental cars and hotels and land exciting discounts. You're not restricted to hotels, though. We have island villas, cabins in the mountains and even castles and houseboats!

Can I choose my airline with an Overland Expedia vacation package?

Yes — and it's simple too. Expedia has access to more than 550 partner airlines throughout the world. Our vacation packages give you the freedom to take your pick of available flight, hotel or activity options that suit you.

If I'm not able to travel, can I cancel my Overland vacation package?

Certainly, and we're here to help. You may be able to cancel or change your Overland vacation package at no cost within 24 hours of booking. However, you may be charged a fee by your airline, hotel or car rental company if you booked more than 24 hours ago. If life gets in the way of your vacation, take a look at our Customer Service Portal for more information.

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