South Side Vacations from $459

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Your South Side Vacation

Discover all the amazing things this neighborhood has to offer with a tailor-made South Side vacation package. However you see yourself spending your days here, you'll find countless opportunities for fun, adventure and relaxation. Some nearby attractions to visit during your trip to South Side include MetraPark, First Interstate Arena and Rocky Mountain College. No matter what your dream South Side vacation may look like, you can turn it into reality with Expedia.

The Latest South Side Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Western Executive Inn

Western Executive Inn

West End
$459
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Billings (BIL)
8/10 Very Good! (535 reviews)
Billings Hotel and Convention Center

Billings Hotel and Convention Center

Southwest Corridor
$572
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Billings (BIL)
8.2/10 Very Good! (1,870 reviews)
Northern Hotel

Northern Hotel

Downtown Billings
$617
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Billings (BIL)
9.6/10 Exceptional! (1,305 reviews)
I have a few things to say. I got 2 rooms. One room neither outlet on lamps worked and there was hair in the shower. The other room the outlet on one of the lamps didn't work. The door the armoire needed WD40 or something. Sounded awful when we opened them. A couple more reasons for overall not coming back: the windows allow for every single noise down below on the streets to be heard in the room. And I mean every noise. Also, there are no mini fridges. That is just a must in this day in age. The gal that checked us in could use some customer service training. Now, the absolute BEST thing you have going for you is, Roy and the rest of the doorman staff. Honestly, Roy is the most kind, young gentleman. His parents should be proud! He is a true gem in his generation.

Reviewed on Oct 6, 2026

Locomotive Inn

Locomotive Inn

$511
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Billings (BIL)
9/10 Wonderful! (316 reviews)
Ledgestone Suites Hotel Billings

Ledgestone Suites Hotel Billings

Southwest Corridor
$527
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Billings (BIL)
9.2/10 Wonderful! (1,489 reviews)

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
A rocky landscape with a wooden walkway, trees, and a river in the background.

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
A steel bridge over a river with a sunset sky.

Downtown Billings

5 out of top 10 points of interest in this area

If you're spending some time in Downtown Billings, Skypoint and Alberta Bair Theater are top sights worth seeing.

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A steel bridge over a river with a sunset sky.

Southwest Corridor

While Southwest Corridor isn't home to many top sights, Riverfront Park and Moss Mansion Museum are some notable places to visit nearby.

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A rocky cliff with trees and white flowers.

Billings Heights

While visiting Billings Heights, you might make a stop by sights like Lake Elmo State Park and Jackpot Casino.

Find hotels in Billings Heights
A river flowing through a snowy forest with ice formations.

Central - Terry

If you're spending some time in Central - Terry, Moss Mansion Museum and Copper Creek Casino are top sights worth seeing.

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South Side Hotel Deals

Modern Get Away

Modern Get Away

Billings MT
8/10 Very Good! (11 reviews)
"Comfortable, clean, had everything we needed."

Reviewed on Sep 21, 2026

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Modern Get Away
Kelly Inn Billings Montana

Kelly Inn Billings Montana

5610 South Frontage Road Billings MT
Fully refundableReserve now, pay when you stay
$89 nightly
$100 total
Nov 1 - Nov 2
Total with taxes and fees
Kelly Inn Billings Montana
Western Executive Inn

Western Executive Inn

3121 King Ave W Billings MT
Fully refundableReserve now, pay when you stay
$72 nightly
$82 total
Oct 16 - Oct 17
Total with taxes and fees
Western Executive Inn
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.
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All Inclusive Vacations
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Golf Vacations
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Where to go when
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Honeymoon Vacations
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Solo Vacations

Stay near popular South Side attractions

Billings Depot

7.4/10 (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.
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Western Heritage Center

9.4/10 (8 reviews)
You can spend an afternoon studying the exhibits at Western Heritage Center during your trip to Billings. Check out the lively bars or top-notch restaurants in this family-friendly area.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.