South Side Vacation Packages 2026 from $420

South Side flight + hotel vacation packages

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

Western Executive Inn

West End

$420

per person

Oct 20 - Oct 24

found 17 hours ago

Roundtrip flight included

Denver (DEN) to Billings (BIL)

Free self parking is available and the hotel's front desk is staffed around-the-clock. WiFi in public areas is free. A computer station is also provided.

Billings Hotel and Convention Center

Southwest Corridor

$537

per person

Nov 13 - Nov 16

found 1 day ago

Roundtrip non-stop flight included

San Antonio (SAT) to Billings (BIL)

A casino and a restaurant are featured at this smoke-free hotel. Enjoy the indoor pool and perks like free self parking and a free airport shuttle. You'll appreciate the gym, bar/lounge, and laundry facilities.

Northern Hotel

Downtown Billings

$701

per person

Oct 20 - Oct 24

found 17 hours ago

Roundtrip flight included

Denver (DEN) to Billings (BIL)

This smoke-free hotel features 2 restaurants, a bar/lounge, and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Free parking, a lobby fireplace, and luggage storage are also offered.

Riversage Billings Inn

Downtown Billings

$519

per person

Oct 20 - Oct 24

found 17 hours ago

Roundtrip flight included

Denver (DEN) to Billings (BIL)

A gym, free self parking, and laundry facilities are featured at this hotel. Guests will appreciate free perks like buffet breakfast and WiFi in public areas. A fireplace in the lobby is provided and the front desk is staffed around-the-clock.

Locomotive Inn

$489

per person

Oct 20 - Oct 24

found 17 hours ago

Roundtrip flight included

Denver (DEN) to Billings (BIL)

This motel features a gym and a hot tub. Enjoy the steam room and free perks like continental breakfast and free self parking. Free WiFi in public areas, a computer station, and laundry facilities are also on offer.

Top South Side hotels deals

Modern Get Away

Billings MT

Get rates

This apartment features laundry facilities.

Kitchen

Washer

Kelly Inn Billings Montana

5610 South Frontage Road Billings MT

Free Cancellation

Reserve now, pay when you stay

$105 nightly

$122 total

Oct 4 - Oct 5

Total with taxes and fees

This hotel features an indoor pool and a 24-hour gym. Enjoy the hot tub and free perks like continental breakfast and free self parking. A 24-hour business center, free WiFi in public areas, and a lobby fireplace are also on offer.

Pool

Hot Tub

Billings Hotel and Convention Center

1223 Mullowney Ln Billings MT

Free Cancellation

Reserve now, pay when you stay

$124 nightly

$137 total

Sep 14 - Sep 15

Total with taxes and fees

A casino and a restaurant are featured at this smoke-free hotel. Enjoy the indoor pool and perks like free self parking and a free airport shuttle. You'll appreciate the gym, bar/lounge, and laundry facilities.

Pool

Hot Tub

Western Executive Inn

3121 King Ave W Billings MT

Free Cancellation

Reserve now, pay when you stay

$64 nightly

$73 total

Oct 2 - Oct 3

Total with taxes and fees

Free self parking is available and the hotel's front desk is staffed around-the-clock. WiFi in public areas is free. A computer station is also provided.

Pet friendly

Parking included

Northern Hotel

19 North Broadway Billings MT

Free Cancellation

Reserve now, pay when you stay

$185 nightly

$204 total

Oct 2 - Oct 3

Total with taxes and fees

This smoke-free hotel features 2 restaurants, a bar/lounge, and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Free parking, a lobby fireplace, and luggage storage are also offered.

Free airport shuttle

Parking included

Dude Rancher Lodge

415 N 29th St Billings MT

Free Cancellation

Reserve now, pay when you stay

$89 nightly

$100 total

Sep 18 - Sep 19

Total with taxes and fees

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the 24-hour business center. Free parking, a lobby fireplace, and a library are also offered.

Pet friendly

Parking included

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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.

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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Frequently asked questions

How much are vacation packages to South Side?

Your travel fantasies can be realized in South Side for as little as $420. Our vacation packages include flights and hotels, and they'll make your booking a cinch. The only thing you'll need to concentrate on is having a good time.

Where can I get the best vacation package deals for South Side?

Scoring the perfect package deal to South Side is easy with Travelocity. With as many as 400 partner airlines and 1,000,000 properties across the globe, you'll have loads of choice when it comes to picking your hotels and flights.

Why should I purchase my South Side vacation bundle via Travelocity?

Incredible savings, loads of exciting destinations and 24/7 customer service you can rely on — that's why. And with our Price Match Guarantee, you can rest easy knowing that you'll always score the best possible deal with Travelocity.

Can I save money on my South Side car rental if I book it with hotels and flights?

You certainly can with our South Side vacation packages. With one of these, there are lots of ways to make your travel budget go further. Combine any two or more car, flight, hotel and tour bookings and watch your savings start to pile up. With your own ride, all the popular sights around South Side are an unforgettable road trip away.

What is there to do in South Side?

It's not difficult to find interesting things to do in this neighborhood. Western Heritage Center is a well-known attraction that lures many visitors.