Roundup Vacation Packages 2026 from $635

Roundup flight + hotel vacation packages

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

Western Executive Inn

West End

$635

per person

Dec 25 - Dec 30

found 5 hours ago

Roundtrip non-stop flight included

St. Louis (STL) 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

$787

per person

Dec 25 - Dec 30

found 5 hours ago

Roundtrip non-stop flight included

St. Louis (STL) 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

$894

per person

Dec 25 - Dec 30

found 5 hours ago

Roundtrip non-stop flight included

St. Louis (STL) 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.

Locomotive Inn

$713

per person

Dec 25 - Dec 30

found 5 hours ago

Roundtrip non-stop flight included

St. Louis (STL) 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.

Ledgestone Suites Hotel Billings

Southwest Corridor

$739

per person

Dec 25 - Dec 30

found 5 hours ago

Roundtrip non-stop flight included

St. Louis (STL) to Billings (BIL)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Traveling on business? Take advantage of the business center and onsite conference space. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.

Top Roundup hotels deals

Autumn's Inn Roundup MT near Hwy 12

630 Main Street Roundup MT

$70 nightly

$76 total

Nov 1 - Nov 2

Total with taxes and fees

A restaurant and free WiFi in public areas are featured at this motel. Guests will appreciate freebies like continental breakfast and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.

Breakfast included

Pet friendly

Montana Country Retreat w/ Hot Tub-Near Lewistown

Grass Range MT

Get rates

A hot tub is featured at this vacation home, along with a garden and laundry facilities.

Hot Tub

Kitchen

Near Hunting: Cozy Cabin w/ Deck in Grass Range!

Grass Range MT

Get rates

Free WiFi in public areas is available at this cottage. Take advantage of the free self parking.

Kitchen

Parking included

Tiny House in the country, close to Billings

Worden MT

Get rates

Stay at this apartment in Worden. Enjoy an in-room coffeemaker and air conditioning.

Kitchen

Air conditioning

Small Town Big Sky

Winnett MT

Get rates

This vacation home features a garden, laundry facilities, and barbecue grills.

Pool

Kitchen

Near Hunting: Cozy Cabin w/ Deck in Grass Range!

Grass Range MT

Get rates

A garden is available at this cabin.

Kitchen

Outdoor Space

Don't see what you're looking for?

See all available properties in Roundup

View all properties

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 Roundup attractions

Roundup City Park

8.0/10 (5 reviews)

Explore the great outdoors at Roundup City Park, a lovely green space in Roundup. Take in the museums while you're in the area.

See properties

Frequently asked questions

How much are vacation packages to Roundup?

Adventure awaits in Roundup, with Travelocity vacation packages starting from just $635. Offering both hotels and flights, these awesome deals are an easy way to discover all corners of the world.

How long should my Roundup vacation be?

Many travelers like to stay around 2 nights in Roundup. But that's only a guide. Whether you prefer to stay for a couple of days or a couple of weeks, you'll love discovering all the fantastic things that this place has to offer.

Where can I get the best vacation package deals for Roundup?

Travelocity can help you lock in a Roundup package deal. With more than 400 air carriers and 1,000,000 properties around the world, we know you'll be able to craft the perfect itinerary.

Why should I book my Roundup vacation package via Travelocity?

From amazing destinations to one-of-a-kind experiences, we have everything you need to satisfy your love for travel. Our friendly 24/7 customer support will also make sure you're taken care of during your trip. And don't panic if you find a better price on your booking, we'll match it. That's our Price Match Guarantee.

Can I save money on my Roundup car rental if I bundle it with hotels and flights?

Combining your bookings into a Roundup vacation package will leave you with a nice chunk of spare change. You can choose a car and flight; a hotel, flight and car; or a car and hotel. You won't find a better way to explore the greater Roundup area than with your own ride. You can also add tours and experiences to your Travelocity package.

Which airport is best for Roundup?

Roundup has two airports to pick from — Logan Intl. Airport (BIL) (45 mi away from the city center) and Lewistown, MT (LWT-Lewistown Municipal) (60 mi away from central Roundup).

Where should I stay when visiting Roundup?

The Autumns Inn is the number one choice of many visitors. Book now before it's too late.