A river with a rocky cliff and trees in the foreground.

South Side Vacations from $835

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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.
  • A fire pit with chairs around it, a pond, and a lodge in the background.
    Jan 5 - Jan 8

    Rock Creek Resort + Flight

    Red Lodge
    3 nights
    3.5 star property
    9.6/10 - Exceptional (234 reviews)
    Roundtrip • Pittsburgh (PIT) - Billings (BIL)
    PIT - COD • 1 stop COD - PIT • 1 stop
    $888
    $835
    per traveler
    found 1 day ago
    Rock Creek Resort
  • A restaurant with outdoor seating, stone accents, and a clear sky.
    Jan 5 - Jan 8

    Quality Inn Red Lodge Gateway To Yellowstone + Flight

    Red Lodge
    3 nights
    2.5 star property
    8.8/10 - Excellent (840 reviews)
    Roundtrip • Pittsburgh (PIT) - Billings (BIL)
    PIT - COD • 1 stop COD - PIT • 1 stop
    $913
    $888
    per traveler
    found 1 day ago
    Quality Inn Red Lodge Gateway To Yellowstone
  • A wooden bear sculpture on a rock formation with a building in the background.
    Jan 5 - Jan 8

    Beartooth Hideaway Inn and Cabins + Flight

    Red Lodge
    3 nights
    2.5 star property
    8.8/10 - Excellent (1,151 reviews)
    Roundtrip • Pittsburgh (PIT) - Billings (BIL)
    PIT - COD • 1 stop COD - PIT • 1 stop
    $872
    $852
    per traveler
    found 1 day ago
    Beartooth Hideaway Inn and Cabins
  • A wooden cabin kitchen with a central island, stainless steel appliances, and a large window offering a view.
    Jan 5 - Jan 8

    Mountain Cabin Near Trails, Skiing & Yellowstone 3 Bedroom Cabin + Flight

    Belfry
    3 nights
    3.0 star property
    10/10 - Exceptional (1 review)
    Roundtrip • Pittsburgh (PIT) - Billings (BIL)
    PIT - COD • 1 stop COD - PIT • 1 stop
    $1,149
    $1,137
    per traveler
    found 1 day ago
    Mountain Cabin Near Trails, Skiing & Yellowstone 3 Bedroom Cabin

Where to stay in South Side

Find the best South Side areas and neighborhoods for the activities you enjoy most.
A rocky landscape with a wooden walkway, trees, and a river in the background.

West End

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

A steel bridge over a river with a sunset sky.

Downtown Billings

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

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.

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.

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.

Discover the most popular places to visit in South Side

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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South Side Hotel Deals

A spacious indoor area with a large tree, a fireplace, and seating arrangements.

Best Western Plus Clocktower Inn

Best Western Plus Clocktower Inn
2.5 star property
North Park, 0.6 mi from South Side
9.0 out of 10, Wonderful, (1,002 reviews)
"The front desk staff couldn’t have been more helpful. We had a problem with the heat in our room and they moved us seamlessly. Cody was one of the most engaging and helpful people I’ve met. No drama, not questions, just helpful."
$119 nightly
The price is $133
Nov 15 - Nov 16
Total with taxes and fees
Best Western Plus Clocktower Inn
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.
See all properties in South Side
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.