Cumberland Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

    deals illustration

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    stays illustration

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration

    Rest easy

    Plan, book, and manage your trip all in one place

Your Cumberland Vacation

When you organize a vacation package to Cumberland, you can relax and enjoy your getaway knowing that all your travel plans have been made in advance. Discover the many gems of this city while based in a neighborhood like Lockerbie Square, which is good for history. If taking in sights is on the cards during your trip to Cumberland, stop by popular attractions like Post Road Recreation Center, Indiana Avenue Historic District and Mid-America Motorcycle Speedway. Whoever you're taking time off with and whatever the size of your budget, your dream Cumberland vacation is just a few clicks away with Expedia.

Top Holiday Package Deals in Cumberland

Price found within the past 48 hours. Click for updated prices.
Crowne Plaza Indianapolis-Dwtn-Union Stn by IHG

Crowne Plaza Indianapolis-Dwtn-Union Stn by IHG

3.5 out of 5
Downtown Indianapolis
per person
Oct 6 - Oct 9
found 10 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Indianapolis (IND)
8.6/10 Excellent! (1,020 reviews)
Love the unique style and the ghost people. Very clean. Will definitely stay again.

Reviewed on Jul. 13, 2025

Embassy Suites by Hilton Indianapolis Downtown

Embassy Suites by Hilton Indianapolis Downtown

3.5 out of 5
Downtown Indianapolis
per person
Oct 6 - Oct 9
found 10 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Indianapolis (IND)
8.4/10 Very Good! (1,002 reviews)
Awesome stay with great amenities!

Reviewed on Jul. 13, 2025

Hyatt House Indianapolis Downtown

Hyatt House Indianapolis Downtown

3 out of 5
Downtown Indianapolis
per person
Oct 6 - Oct 9
found 10 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Indianapolis (IND)
9/10 Wonderful! (1,006 reviews)
The staff was wonderful and the breakfast was amazing

Reviewed on Jul. 13, 2025

Hyatt Place Indianapolis Downtown

Hyatt Place Indianapolis Downtown

3 out of 5
Downtown Indianapolis
per person
Oct 6 - Oct 9
found 10 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Indianapolis (IND)
8.8/10 Excellent! (1,171 reviews)
Excellent hotel, great location.

Reviewed on Jul. 13, 2025

Ironworks Hotel Indy

Ironworks Hotel Indy

4 out of 5
per person
Oct 6 - Oct 9
found 10 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Indianapolis (IND)
9.8/10 Exceptional! (1,489 reviews)
Great stay! Nice hotel and alot to do near the property. We had zero issues. Will stay again

Reviewed on Jul. 13, 2025

Where to stay in Cumberland

Find the best Cumberland areas and neighborhoods for the activities you enjoy most. Learn more about Cumberland
Central Canal which includes landscape views, a river or creek and a city

Downtown Indianapolis

5 out of top 10 points of interest in this area
4.5/5(57 area reviews)

As the city's cultural, political, and economic hub, this neighborhood boasts historic districts, performing arts venues, and museums. Enjoy nightlife on Meridian Street and Massachusetts Avenue, or stroll along the Indianapolis Canal Walk.

Find hotels in Downtown Indianapolis

Cumberland Hotel Deals

Wyndham Indianapolis Airport
Wyndham Indianapolis Airport
3.5 out of 5
2544 Executive Dr, Indianapolis, IN
Fully refundableReserve now, pay when you stay
The price is CA $150 per night from Aug 4 to Aug 5
CA $150
CA $176 total
Aug 4 - Aug 5
includes taxes & fees
7.8/10 Good! (1,257 reviews)
Fever game
"The hotel location made for easy access to downtown area. Rooms were clean with comfortable beds. The sinks and toilets were low and we would have liked them higher. Great place to stay overall?"

Reviewed on Jul. 10, 2025

Wyndham Indianapolis Airport
Ironworks Hotel Indy
Ironworks Hotel Indy
4 out of 5
2721 E 86th Street, Indianapolis, IN
Fully refundableReserve now, pay when you stay
The price is CA $245 per night from Jul 14 to Jul 15
CA $245
CA $287 total
Jul 14 - Jul 15
includes taxes & fees
9.6/10 Exceptional! (1,507 reviews)
"Only issue was Keurig in room 203 did not brew the coffee. water was added and it just dripped."

Reviewed on Jul. 13, 2025

Ironworks Hotel Indy
Sheraton Indianapolis Hotel at Keystone Crossing
Sheraton Indianapolis Hotel at Keystone Crossing
4 out of 5
8787 Keystone Crossing, Indianapolis, IN
The price is CA $151 per night from Jul 14 to Jul 15
CA $151
CA $176 total
Jul 14 - Jul 15
includes taxes & fees
8.6/10 Excellent! (1,264 reviews)
"Would stay again"

Reviewed on Jul. 9, 2025

Sheraton Indianapolis Hotel at Keystone Crossing
See all 2,363 properties in Cumberland
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Cumberland vacation package cost?
Cross off another part of the world with our Cumberland vacation packages, which start from a low CA $1,100. Select the flights and hotels that fit your travel plans. Then, add on one or two experiences or tours for a memorable adventure.
How do I get a cheap travel package to Cumberland?
Our Cumberland vacation packages promise plenty of savings for the savvy wanderer. For the best deals, simply combine your hotel, flights and extras (including tours) into a handy package. But cheap prices are only the start of your next epic adventure. Book with Expedia and and you'll have over 550 air carriers and 1,000,000 hotels across the globe to choose from. Whatever your budget, there's a package here just for you.
Where should I stay in Cumberland?
Make sightseeing easy by staying someplace within walking distance of Cumberland's big attractions. Indianapolis Motor Speedway and Lucas Oil Stadium are two of the best in the area.
What are the top hotels in Cumberland?
When it comes to comfy places to stay in Cumberland, you can't beat Admiral Motel. Have a look at our offers and score a great price.
How far in advance should I book my Cumberland vacation?
To land rock-bottom prices, book ASAP. Airlines usually release tickets, along with some of the lowest fares, nearly a year prior to departure. Hotels, car rental and experiences should also be booked early so you can have the pick of the bunch. If you're in need of a last-minute getaway in Cumberland, there are always plenty of great deals to be had on Expedia. Check them out now!
What does an Expedia Cumberland travel package include?
It comes down to what you're looking for. If you're traveling by yourself, you might decide to bundle flights and hotels. Bringing the entire family to Cumberland? A travel package including hotels, flights and rental cars might suit you better. Expedia gives you the freedom to customize your travel package.
What should I know before booking a Cumberland travel package?
Whether it's relaxation or adventure you're chasing, a Cumberland vacation package lets you organize your escape your way. Plus, you'll get access to great discounts just for combining your hotel with your flights and rental car. The more you bundle, the more you'll save!
Can I choose my airline with a Cumberland Expedia vacation package?
You can. We have more than 550 partner airlines globally, so select the carrier that suits your travel needs.
If I'm not able to travel, can I cancel my Cumberland vacation package?
Yes, it's possible to cancel your Cumberland booking if your travel plans have been upended. Whether you'll be charged a fee or not depends on your airline, hotel or car rental company. You may be able to cancel or change your booking for free if you booked in the last 24 hours. Visit our Customer Service Portal to learn more.

Discover the most popular places to visit in Cumberland

Indianapolis Motor Speedway which includes interior views

Indianapolis Motor Speedway

4.5/5(26 reviews)

Buckle up at the world’s most famous speedway and experience G-force thrills usually reserved for race car drivers.

Indianapolis Motor Speedway
Indiana Convention Center

Indiana Convention Center

4/5(24 reviews)

During your trip, find out what's happening at Indiana Convention Center, a top convention center in Indianapolis. Experience the area's acclaimed theater scene and entertainment choices.

Indiana Convention Center
Gainbridge Fieldhouse

Gainbridge Fieldhouse

3.5/5(5 reviews)

Catch an event at Gainbridge Fieldhouse during your trip to Indianapolis. Experience the area's entertainment choices or attend a sporting event.

Gainbridge Fieldhouse

Things to do

Step into the shadows and discover the haunting tales of our city's past.

Indianapolis Ghosts: Haunts, Spirits, and Phantoms Walking Tour

CA $44
per adult
Indianapolis Ghosts: Haunts, Spirits, and Phantoms Walking Tour
Group with axes for throwing in Indianapolis

30-Minute Walk-In Axe Throwing Experience Indianapolis

CA $30
per adult
100% of travellers recommend
30-Minute Walk-In Axe Throwing Experience Indianapolis
Bike and Brews Seeing Indy on an E-Bike

Bike and Brews Seeing Indy on an E-Bike

CA $191
per adult
Bike and Brews Seeing Indy on an E-Bike
See all activities in Indianapolis
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.