South Side Vacation Packages

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Top Holiday Package Deals in South Side

Price found within the past 48 hours. Click for updated prices.
Hardin Lodge By Capital O Little Bighorn Battlefield I-90

Hardin Lodge By Capital O Little Bighorn Battlefield I-90

2.5 out of 5
per person
Aug 30 - Sep 3
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Billings (BIL)
7.6/10 Good! (84 reviews)
Front desk staff was super nice and helpful!

Reviewed on Jul. 11, 2025

Billings Hotel and Convention Center

Billings Hotel and Convention Center

3 out of 5
per person
Aug 30 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Billings (BIL)
8/10 Very Good! (1,163 reviews)
Older property with very few amenities (little things). No soap for the sink. No lids for coffee cups. Beds not very comfortable, feel old. Problems with check in.

Reviewed on Jul. 16, 2025

DoubleTree by Hilton Hotel Billings

DoubleTree by Hilton Hotel Billings

4 out of 5
North Park
per person
Aug 30 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Billings (BIL)
8.2/10 Very Good! (1,001 reviews)
Central location plenty of bars and restaurants.

Reviewed on Jun. 28, 2025

Northern Hotel

Northern Hotel

4 out of 5
per person
Aug 30 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Billings (BIL)
9.4/10 Exceptional! (1,045 reviews)
Friendly staff, clean, spacious

Reviewed on Jul. 16, 2025

Courtyard BY Marriott Billings

Courtyard BY Marriott Billings

3 out of 5
per person
Aug 30 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Billings (BIL)
10/10 Exceptional! (9 reviews)
Very clean, modern rooms.

Reviewed on Apr. 26, 2025

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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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 Lucky Lil's Casino are top sights worth seeing.

Find hotels in West End

South Side Hotel Deals

Super 8 by Wyndham Billings

Super 8 by Wyndham Billings

2 out of 5
5400 Southgate Dr, Billings, MT
Fully refundableReserve now, pay when you stay
The price is CA $122 per night from Aug 3 to Aug 4
CA $122
CA $137 total
Aug 3 - Aug 4
includes taxes & fees
7.8/10 Good! (1,425 reviews)
"Met our expectations for a quick place to spend the night on our cross country trip."

Reviewed on Jul. 16, 2025

Super 8 by Wyndham Billings
Quality Inn

Quality Inn

2.5 out of 5
2036 Overland Ave, Billings, MT
Fully refundableReserve now, pay when you stay
The price is CA $131 per night from Jul 27 to Jul 28
CA $131
CA $147 total
Jul 27 - Jul 28
includes taxes & fees
8.2/10 Very Good! (1,018 reviews)
"Convenient for us and our owts"

Reviewed on Jul. 12, 2025

Quality Inn
Kelly Inn Billings Montana

Kelly Inn Billings Montana

2.5 out of 5
5610 South Frontage Road, Billings, MT
Fully refundable
The price is CA $152 per night from Jul 27 to Jul 28
CA $152
CA $170 total
Jul 27 - Jul 28
includes taxes & fees
8.4/10 Very Good! (1,661 reviews)
"Construction"

Reviewed on Jul. 16, 2025

Kelly Inn Billings Montana
See all 262 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 $934. 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

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 lively bars or top-notch restaurants in this romantic area.

ZooMontana

Rocky Mountain College

3.5/5(2 reviews)

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

Rocky Mountain College

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 lively bars in this family-friendly area.

Rimrock Mall

Things to do

Self-Guided Scavenger Hunt: Bountiful Billings

Self-Guided Scavenger Hunt: Bountiful Billings

CA $17
per adult
Self-Guided Scavenger Hunt: Bountiful Billings
See all activities in Billings
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.