Roundup Vacation Packages 2026 from $618

Roundup flight + hotel vacation packages

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

Billings Hotel and Convention Center

$618

per person

Jul 8 - Jul 12

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) 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

$765

per person

Jul 8 - Jul 12

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) 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.

Ledgestone Suites Hotel Billings

$685

per person

Jul 8 - Jul 12

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) 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. A 24-hour gym, a computer station, and laundry facilities are also on offer.

Comfort Suites Billings

$710

per person

Jul 8 - Jul 12

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to Billings (BIL)

This hotel features an indoor pool and a hot tub. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Hilltop Inn by Riversage

Downtown Billings

$677

per person

Jul 8 - Jul 12

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) 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 and dry cleaning are also provided.

Top Roundup hotels deals

Autumn's Inn

630 Main Street Roundup MT

Free Cancellation

Reserve now, pay when you stay

$75 nightly

$81 total

Apr 14 - Apr 15

Total with taxes and fees

This motel features free WiFi in public areas, barbecue grills, and free self parking. Enjoy the free continental breakfast each morning. A garden and a picnic area are also provided.

Breakfast included

Pet friendly

Montana Country Retreat w/ Hot Tub-Near Lewistown

Grass Range MT

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

Hot Tub

Pet friendly

See the stars from this cozy guest cabin 30 minutes from Billings.

Shepherd MT

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Stay at this cabin in Shepherd. Enjoy free WiFi, an in-room coffeemaker, and air conditioning.

Kitchen

Free WiFi

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

Grass Range MT

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

Kitchen

Parking included

Small Town Big Sky

Winnett MT

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

Pool

Kitchen

Tiny House in the country, close to Billings

Worden MT

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

Kitchen

Air conditioning

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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.

Popular places to visit

Roundup City Park

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

Pine Ridge Golf Club

Enjoy a round of golf in Camp Three at Pine Ridge Golf Club. Amble around the area's parks or experience its museums.

Roundup Memorial Healthcare

Though Roundup Memorial Healthcare might be what brings you to town, perhaps you'll have a chance to explore more of Roundup while you are here.

Frequently asked questions

How much are vacation packages to Roundup?

Adventure awaits in Roundup, with Travelocity vacation packages starting from just $618. 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.