South Side Vacations from $314

Book a Hotel + Flight or Car together to unlock savings

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.
Howard Johnson by Wyndham Billings

Howard Johnson by Wyndham Billings

2 out of 5
Price was $391, price is now $314 per person
$314
per person
Nov 17 - Nov 21
found 1 day ago
Roundtrip flight included
Portland (PDX) to Billings (BIL)
5.8/10 (1,008 reviews)
Check in was great, very polite young man working the desk. Room is clean but beds are squeaky and pillows are timy

Reviewed on Aug 31, 2025

Billings Hotel and Convention Center

Billings Hotel and Convention Center

3 out of 5
Price was $935, price is now $674 per person
$674
per person
Oct 1 - Oct 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Billings (BIL)
8/10 Very Good! (1,270 reviews)
Quiet clean but needs updates Lots of spiders and flying ants in our room

Reviewed on Aug 30, 2025

SureStay Plus Hotel by Best Western Billings

SureStay Plus Hotel by Best Western Billings

2.5 out of 5
Price was $508, price is now $403 per person
$403
per person
Nov 17 - Nov 21
found 1 day ago
Roundtrip flight included
Portland (PDX) to Billings (BIL)
8.8/10 Excellent! (1,012 reviews)
The hot tub was warm, at most, with blasts of coolness. Air in room was warm during the night, air conditioner was inconsistent.

Reviewed on Aug 28, 2025

Northern Hotel

Northern Hotel

4 out of 5
Price was $761, price is now $625 per person
$625
per person
Nov 6 - Nov 9
found 21 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Billings (BIL)
9.6/10 Exceptional! (1,077 reviews)
Bernie’s is terrific!

Reviewed on Aug 30, 2025

Ledgestone Suites Hotel Billings

Ledgestone Suites Hotel Billings

2.5 out of 5
Price was $501, price is now $414 per person
$414
per person
Nov 17 - Nov 21
found 1 day ago
Roundtrip flight included
Portland (PDX) to Billings (BIL)
9.4/10 Exceptional! (1,190 reviews)
Basic, comfortable room. Very clean, comfortable beds. Would stay there again.

Reviewed on Sep 1, 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

Kelly Inn Billings Montana

Kelly Inn Billings Montana

2.5 out of 5
5610 South Frontage Road, Billings, MT
Fully refundable
$118 nightly
The price is $132 total per night from Sep 30 to Oct 1
$132 total
Sep 30 - Oct 1
Total with taxes and fees
Kelly Inn Billings Montana
Woodspring Suites Billings

Woodspring Suites Billings

2.5 out of 5
4750 King Ave East, Billings, MT
Fully refundableReserve now, pay when you stay
$79 nightly
The price is $89 total per night from Sep 2 to Sep 3
$89 total
Sep 2 - Sep 3
Total with taxes and fees
Woodspring Suites Billings
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
$133 nightly
The price is $147 total per night from Sep 29 to Sep 30
$147 total
Sep 29 - Sep 30
Total with taxes and fees
8/10 Very Good! (1,195 reviews)
"Quiet clean but needs updates Lots of spiders and flying ants in our room"

Reviewed on Aug 30, 2025

Billings Hotel and Convention Center
See all 249 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
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in South Side

Billings Depot

You can learn about the history of Billings when you stop by Billings Depot. Check out the lively bars or top-notch restaurants in this family-friendly area.

Billings Depot

MetraPark

Catch an event at MetraPark during your trip to Billings. Check out the top-notch restaurants or lively bars in this family-friendly area.

MetraPark

Reef Indoor Water Park

Bring the kiddos to Reef Indoor Water Park and enjoy this exciting theme park in Billings. Check out the lively bars or top-notch restaurants in this romantic area.

Reef Indoor Water Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.