Roundup Vacations 2026 from CA $1,409

Roundup flight + hotel packages

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

Beartooth Hideaway Inn and Cabins

CA $1,409

per person

Dec 19 - Dec 23

found 1 day ago

Roundtrip flight included

London (YXU) to Billings (BIL)

Stay at this hotel in Red Lodge. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Lake Fork Trail and Montana Candy Emporium are located nearby.

Rock Creek Resort

CA $1,505

per person

Dec 19 - Dec 23

found 1 day ago

Roundtrip flight included

London (YXU) to Billings (BIL)

Stay at this lodge in Red Lodge. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Nichols Creek Trailhead and Lake Fork Trail are located nearby.

Top Roundup hotels deals

Autumn's Inn

630 Main Street Roundup MT

Free cancellation

Reserve now, pay when you stay

CA $87

CA $94 total

Oct 4 - Oct 5

includes taxes & fees

Book a stay at this business-friendly motel in Roundup. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Musselshell Valley Historical Museum and Roundup City Park are located nearby.

Breakfast included

Pet-friendly

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

Montana Country Retreat w/ Hot Tub-Near Lewistown

Grass Range MT

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Stay at this vacation home in Grass Range. Enjoy free WiFi, a garden, and laundry facilities.

Hot tub

Kitchen

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

Grass Range MT

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Stay at this cottage in Grass Range. Enjoy free parking and in-room fireplaces.

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.

Small Town Big Sky

Winnett MT

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Stay at this vacation home in Winnett. Enjoy free WiFi, a garden, and laundry facilities.

Pool

Kitchen

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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 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.

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Roundup Vacations

Are you all set for your next great adventure? Ensure you don't miss out on any excitement in Roundup by learning a few things about it before you hurry off.

You'll find this town in South Central Montana, and just 2 miles (3 kilometers) away from Camp Three.

Approximately 2,000 people reside in this part of South Central Montana, so there are loads of opportunities to make new friends.

Places to visit in Roundup

Even on a rainy day, it's worth taking a stroll through Roundup City Park. Pop open your umbrella and soak up the fresh earthy smell. Need some more options? Ditch the history books! Let the past jump off the page at Musselshell Valley Historical Museum. And there's more. Wriggle into your finest khakis and grab your best driver. If you're to itching to head outdoors for an afternoon on the green, secure a tee time at Pine Ridge Golf Club.

Where do you fly into for Roundup?

Seats in the upright position, stow your tray tables and get set to experience Roundup! Once the wheels hit the runway at Logan International Airport (BIL), the happening main streets will be just 45 miles (72 kilometers) north of here.

Frequently asked questions

How much are vacation packages to Roundup?

Adventure awaits in Roundup, with Travelocity vacation packages starting from just CA $1,409. 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) (72 kilometers away from the city center) and Lewistown, MT (LWT-Lewistown Municipal) (97 kilometers 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.