South Side Holidays

Book a Hotel + Flight or Car together to unlock savings

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

While visiting West End, you might make a stop by sights like Rimrock Mall and Lucky Lil's Casino.

Find hotels in West End

Top hotels in South Side

Kelly Inn Billings Montana

Kelly Inn Billings Montana

2.5 out of 5
5610 South Frontage Road Billings MT
Fully refundable
The price is 2.960.624 ₫ per night from 7 Jun to 8 Jun
2.960.624 ₫
3.302.771 ₫ total
7 Jun - 8 Jun
includes taxes & fees
8.8/10 Excellent! (1,883 reviews)
"We upgraded our room at check-in. The man at the front desk was very nice and we appreciated his help."

Reviewed on 2 Jun 2026

Kelly Inn Billings Montana
Billings Hotel and Convention Center

Billings Hotel and Convention Center

3 out of 5
1223 Mullowney Ln Billings MT
The price is 3.125.382 ₫ per night from 3 Jun to 4 Jun
3.125.382 ₫
3.612.285 ₫ total
3 Jun - 4 Jun
includes taxes & fees
8.2/10 Very Good! (1,593 reviews)
"Shower pressure was a little low but other than that, great stay!!!!"

Reviewed on 1 Jun 2026

Billings Hotel and Convention Center
Dude Rancher Lodge

Dude Rancher Lodge

3 out of 5
415 N 29th St Billings MT
The price is 2.512.365 ₫ per night from 3 Jun to 4 Jun
2.512.365 ₫
2.818.648 ₫ total
3 Jun - 4 Jun
includes taxes & fees
8.6/10 Excellent! (1,174 reviews)
"Clean room, friendly staff, air conditioner didn't work in our room and the tub drained slowly. The breakfast was incredible though and cheap. An $8 breakfast voucher got me a loaded breakfast burrito that was oh so delicious!!"

Reviewed on 1 Jun 2026

Dude Rancher Lodge
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.

Frequently asked questions

How much does a South Side holiday package cost?
From just . 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 1null000null000 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 holiday 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 holiday?
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 holiday 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, cosy city apartments and even ranches and treehouses!
Can I choose my airline with a South Side Expedia holiday 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 holiday package?
Your situation can change without warning, so yes, you can. You may be able to cancel or change your South Side holiday 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.

Popular places to visit

Colorado School of Mines Administration Building on a sunny day

Rocky Mountain College

Enjoy the student vibe at Rocky Mountain College during your visit to Billings. Visit the top-notch restaurants or lively bars in this family-friendly area.

Rocky Mountain College

Billings Depot

You can learn about the history of Billings with a trip to Billings Depot. Visit the lively bars or top-notch restaurants in this family-friendly area.

Billings Depot

Western Heritage Center

You can spend time exploring the galleries in Western Heritage Center in Billings. Visit the lively bars or top-notch restaurants in this family-friendly area.

Western Heritage Center