South Side Vacation Packages

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

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Top Holiday Package Deals in South Side

Price found within the past 48 hours. Click for updated prices.
Dude Rancher Lodge

Dude Rancher Lodge

3 out of 5
Downtown Billings
Price was CA $828, price is now CA $764 per person
CA $764
per person
Mar 17 - Mar 23
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Billings (BIL)
8.6/10 Excellent! (1,068 reviews)
Always love to come stay here.

Reviewed on Feb 1, 2026

Billings Hotel and Convention Center

Billings Hotel and Convention Center

3 out of 5
Price was CA $1,670, price is now CA $876 per person
CA $876
per person
Mar 17 - Mar 23
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Billings (BIL)
8/10 Very Good! (1,349 reviews)
Very friendly staff. We will definitely stay there again!

Reviewed on Jan 27, 2026

Northern Hotel

Northern Hotel

4 out of 5
Downtown Billings
Price was CA $1,434, price is now CA $1,079 per person
CA $1,079
per person
Mar 17 - Mar 23
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Billings (BIL)
9.6/10 Exceptional! (1,147 reviews)
I love The Northern! Great location, service, and food. My favorite place to stay in Billings 🌟

Reviewed on Feb 4, 2026

Where to stay in South Side

Find the best South Side areas and neighborhoods for the activities you enjoy most. Learn more about South Side
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Central - Terry

Central - Terry might not have many top sights, but Moss Mansion Museum and Nickels Casino are two attractions nearby that you can check out.

Find hotels in Central - Terry

South Side Hotel Deals

Kelly Inn Billings Montana

Kelly Inn Billings Montana

2.5 out of 5
5610 South Frontage Road Billings MT
Fully refundableReserve now, pay when you stay
The price is CA $117 per night from Feb 8 to Feb 9
CA $117
CA $132 total
Feb 8 - Feb 9
includes taxes & fees
8.6/10 Excellent! (1,856 reviews)
Friendly staff and a clean room. Really enjoyed having an exterior door to the room.

Reviewed on Feb 2, 2026

Kelly Inn Billings Montana
Hyatt Place Billings

Hyatt Place Billings

3 out of 5
705 Henry Chapple Street Billings MT
Fully refundableReserve now, pay when you stay
The price is CA $143 per night from Feb 15 to Feb 16
CA $143
CA $160 total
Feb 15 - Feb 16
includes taxes & fees
9.4/10 Exceptional! (374 reviews)
The hotel and room were clean and comfortable. We enjoyed the pool and the breakfast was delicious. The only drawback was the extremely loud road noise which woke us up all night.

Reviewed on Feb 2, 2026

Hyatt Place Billings
Billings Hotel and Convention Center

Billings Hotel and Convention Center

3 out of 5
1223 Mullowney Ln Billings MT
Fully refundableReserve now, pay when you stay
8/10 Very Good! (1,433 reviews)
Good place to be

Reviewed on Feb 2, 2026

Get rates
Billings Hotel and Convention Center
See all 279 properties in South Side
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 South Side vacation package cost?
From just CA $764. Yes, you read that right. Our South Side packages are the best way to make your budget go further. Bundle your hotels, flights and rental car and discover this exciting destination.
How do I get a cheap travel package to South Side?
You'll save big if you combine your car rentals, hotels and flights into a South Side travel package. Sometimes cheap packages mean fewer choices. But not with Expedia. We offer over 550 air carriers and 1,000,000 hotels throughout the world, so you'll always have plenty of options to choose from. Eager to save even more? Add some interesting activities to your package deal to unlock even more discounts! After all, travel is about more than just getting to your destination.
Where should I stay in South Side?
A vacation in South Side isn't complete without stopping by MetraPark, Rocky Mountain College and First Interstate Arena. Spend your nights near these top sights and make sightseeing simple.
How far in advance should I book my South Side vacation?
Reserving your flights early with Expedia means one less thing to have to worry about. A number of air carriers advertise prices up to a year in advance. This is typically the cheapest time to book. If circumstances have left you booking late, discount flights to South Side occasionally appear just weeks before departure.
What does an Expedia South Side travel package include?
Expedia has all you need to lock in South Side escape, but what your package looks like is your call. Choose from any combination of rental cars, hotels and flights. In search of some tours or experiences to fill in your time? Once you've made your booking, you can add them too. No matter your style, there's a vacation package to meet your needs.
What should I know before booking a South Side travel package?
Get ready to save with an Expedia travel package. Combine your airfares, rental cars and hotels and be rewarded with terrific discounts. You're not limited to hotels, however. Book with us and choose from beachfront villas, cozy city apartments and even ranches and treehouses!
Can I choose my airline with a South Side Expedia vacation package?
Yes, definitely. Expedia has more than 550 partner airlines to pick from globally. With so much choice, finding the ideal carrier to bring you to South Side shouldn't be hard.
If I'm not able to travel, can I cancel my South Side vacation package?
Your situation can change without warning, so yes, you can. You may be able to cancel or change your South Side vacation package for free within 24 hours of booking. For bookings older than that, you can still make changes, but your airline, hotel or car rental company may impose a fee. Looking for more information? Visit our Customer Service Portal. We'll help make sure your trip goes off without a hitch.

Discover the most popular places to visit in South Side

Colorado School of Mines Administration Building on a sunny day

Rocky Mountain College

3.5/5(2 reviews)

Explore the campus of Rocky Mountain College during your stay in Billings. Check out the lively bars or top-notch restaurants in this family-friendly area.

Rocky Mountain College

ZooMontana

4/5(2 reviews)

Why not see the exotic and native animals who call ZooMontana home during your vacation in Billings? Check out the top-notch restaurants or lively bars in this romantic area.

ZooMontana

Rimrock Mall

4/5(11 reviews)

You can find the perfect gifts to bring home at Rimrock Mall during your trip to Billings. Check out the charming coffeehouses or top-notch restaurants in this family-friendly area.

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