South Side Vacation Packages

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  • Better together

    Save up to CA $4,200 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.
Billings Hotel and Convention Center

Billings Hotel and Convention Center

3 out of 5
Southwest Corridor
Price was CA $1,570, price is now CA $1,051 per person
CA $1,051
per person
Sep 8 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Billings (BIL)
8.2/10 Very Good! (1,615 reviews)
Very helpful staff. Great pool!

Reviewed on Jun 17, 2026

Northern Hotel

Northern Hotel

4 out of 5
Downtown Billings
Price was CA $1,393, price is now CA $1,176 per person
CA $1,176
per person
Aug 3 - Aug 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Billings (BIL)
9.6/10 Exceptional! (1,234 reviews)
Clean, quiet, updated and convenient. We really enjoyed our stay at the Northern hotel.

Reviewed on Jun 14, 2026

My Place Hotel - Billings, MT

My Place Hotel - Billings, MT

2 out of 5
Southwest Corridor
Price was CA $1,134, price is now CA $1,053 per person
CA $1,053
per person
Aug 3 - Aug 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Billings (BIL)
8.8/10 Excellent! (955 reviews)
Had a lovely stay. The room was clean. The AC worked great. The beds are comfortable. The staff are kind. Would definitely stay here again!

Reviewed on Jun 18, 2026

Kelly Inn Billings Montana

Kelly Inn Billings Montana

2.5 out of 5
Southwest Corridor
Price was CA $1,182, price is now CA $1,101 per person
CA $1,101
per person
Aug 3 - Aug 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Billings (BIL)
8.8/10 Excellent! (1,896 reviews)
Location, large room clean

Reviewed on Jun 18, 2026

Rock Creek Resort

Rock Creek Resort

4 out of 5
Price was CA $1,443, price is now CA $1,351 per person
CA $1,351
per person
Aug 3 - Aug 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Billings (BIL)
9.8/10 Exceptional! (94 reviews)
Good location . Nice amenities. Didn’t give me good reason booked by Expedia .

Reviewed on Jun 11, 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
Pompeys Pillar National Monument

West End

1 out of top 10 points of interest in this area

If you're spending some time in West End, Rimrock Mall and Onyx Casino are top sights worth seeing.

Find hotels in West End

South Side Hotel Deals

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
The price is CA $167 per night from Jun 28 to Jun 29
CA $167
CA $194 total
Jun 28 - Jun 29
includes taxes & fees
8.2/10 Very Good! (1,618 reviews)
"It's an older facility, but they are doing a great job of upgrading and maintaining it. This was our 2nd stay. The beds were very comfortable. The pool area was clean. The water slides were amazing. My husband and I even went down several times with our kids. There is an enclosed courtyard with a ..."

Reviewed on Jun 18, 2026

Billings Hotel and Convention Center
Dude Rancher Lodge

Dude Rancher Lodge

3 out of 5
415 N 29th St Billings MT
Fully refundableReserve now, pay when you stay
The price is CA $135 per night from Jun 28 to Jun 29
CA $135
CA $151 total
Jun 28 - Jun 29
includes taxes & fees
8.6/10 Excellent! (1,202 reviews)
"Definitely a dated property, but not in a bad way at all. Lots of character, comfortable, and excellent water pressure in the shower. All staff members we interacted with were extremely helpful and friendly. I would definitely stay here again! :-)"

Reviewed on Jun 19, 2026

Dude Rancher Lodge
Hilltop Inn by Riversage

Hilltop Inn by Riversage

3 out of 5
1116 North 28th St. Billings MT
Fully refundableReserve now, pay when you stay
The price is CA $149 per night from Jul 6 to Jul 7
CA $149
CA $166 total
Jul 6 - Jul 7
includes taxes & fees
Hilltop Inn by Riversage
See all 276 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a South Side vacation package cost?
From just CA $1,051. 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.

Stay near popular South Side attractions

Billings Depot

7.4/5 (154 reviews)
You can learn about the history of Billings when you stop by Billings Depot. Check out the top-notch restaurants or lively bars in this family-friendly area.
See properties
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.