Roundup Vacations from $726

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Your Roundup Vacation

The friendly locals and small-town feel are just the start of the things Roundup has going for it. Enjoy the very best of this lively city your way with a customized Roundup vacation package. Fill your spare time with tours of Roundup City Park, Pine Ridge Golf Club and Musselshell Valley Historical Museum, some of the things you should see during your trip to Roundup. Whatever your travel plans or the size of your budget, organizing your ultimate tailored Roundup vacation is simple with Expedia.

The Latest Roundup Vacation Packages

Prices and availability subject to change. Additional terms may apply.
Billings Hotel and Convention Center

Billings Hotel and Convention Center

3 out of 5
per person
Jun 27 - Jun 30
Roundtrip flight included
Dallas (DFW) to Billings (BIL)
8/10 Very Good! (1,001 reviews)
Great place to stay with the kids and staff is always great!

Reviewed on Apr 24, 2024

Northern Hotel

Northern Hotel

4 out of 5
per person
Jun 27 - Jun 30
Roundtrip flight included
Dallas (DFW) to Billings (BIL)
9.2/10 Wonderful! (1,001 reviews)
Loved our stay here, just wish we had more time to enjoy the onsite restaurants. Expedia VIP gave us credit per day, unfortunately, we never were able to use just do to timining. Wish the rooms had fans or white noise machines to allow for a more restful sleep. It was a gorgeous room but the downtown traffic definitely kept us up.

Reviewed on Apr 15, 2024

The Red Lodge Inn

The Red Lodge Inn

3.5 out of 5
per person
Jun 27 - Jun 30
Roundtrip flight included
Dallas (DFW) to Billings (BIL)
9.4/10 Exceptional! (331 reviews)
Very clean and nice staff!

Reviewed on Apr 9, 2024

Kelly Inn Billings Montana

Kelly Inn Billings Montana

2.5 out of 5
per person
Jul 11 - Jul 15
Roundtrip non-stop flight included
Houston (IAH) to Billings (BIL)
8.2/10 Very Good! (1,222 reviews)
A very comfortable one night stop

Reviewed on Apr 24, 2024

Hilltop Inn by Riversage

Hilltop Inn by Riversage

3 out of 5
per person
Jul 11 - Jul 15
Roundtrip non-stop flight included
Houston (IAH) to Billings (BIL)
9/10 Wonderful! (1,271 reviews)
Requested wake-up call for early morning flight but this was not fulfilled.

Reviewed on Apr 20, 2024

Roundup Essential Information

Language
English
Currency
U.S dollars
Population
1,850
Max Temp Winter
30ºF
Max Temp Summer
80ºF
Top Sights
Musselshell Valley Historical Museum, Roundup City Park and Pine Ridge Golf Club

Roundup Hotel Deals

Autumn's Inn
Autumn's Inn
2.5 out of 5
630 Main Street, Roundup, MT
Fully refundableReserve now, pay when you stay
The price is $85 per night from May 2 to May 3
$85
$92 total
includes taxes & fees
May 2 - May 3
8/10 Very Good! (80 reviews)
"Nice"

Reviewed on Mar 4, 2024

Autumn's Inn
"The Dugout" in the Bull Mountains...a quaint little getaway!
"The Dugout" in the Bull Mountains...a quaint little getaway!
Roundup
9.8/10 Exceptional! (28 reviews)
Great place
"We came home for Christmas and this was a great place to stay. It was clean, quiet and easy to keep warm. Beds were comfortable and the living room was a great place to hang out and relax at night."

Reviewed on Dec 26, 2023

Get rates
"The Dugout" in the Bull Mountains...a quaint little getaway!
The Cabin...a cozy little retreat
The Cabin...a cozy little retreat
Roundup
The price is $104 per night from May 1 to May 2
$104
$134 total
includes taxes & fees
May 1 - May 2
9.6/10 Exceptional! (13 reviews)
The cabin outside Roundup
"Cute, comfortable, serene"

Reviewed on Apr 12, 2024

The Cabin...a cozy little retreat
See all 19 properties in Roundup
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.

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Frequently asked questions

How much does a Roundup vacation package cost?
Maybe less than you might think — from only $726, as a matter of fact! By combining flights, hotels and car rentals into your own customized vacation package, your getaway to Roundup is just clicks away.
How do I get a cheap travel package to Roundup?
Bundle your flight and hotel bookings, add on extras such as a rental car or activities, and save with a Roundup vacation package. You won’t just score exciting discounts on your getaway — you’ll have loads of choice too. When you book with Expedia, you’ll have your pick of over 550 airlines and 1,000,000 properties globally. Your next affordable adventure begins right here, right now!
Where should I stay in Roundup?
A trip to Roundup wouldn’t be complete without visiting Pine Ridge Golf Club, Roundup City Park and Roundup Memorial Healthcare. Stay near these top sights and make sightseeing simple.
What are the top hotels in Roundup?
If it’s your first time in Roundup, reserve a room at Comfortable Home In Roundup or Big Sky Motel. Both hotels offer friendly service and are popular options with many savvy travelers.
How far in advance should I book my Roundup vacation?
Be rewarded with the widest variety at the lowest prices by booking your Roundup adventure early. Air carriers tend to sell flights anywhere up to 12 months prior to departure, so start locking things in as soon as you can. That said, Expedia is committed to giving you the best bargains around, so it’s never a bad time to book your dream vacation!
What does an Expedia Roundup travel package include?
Hotels, flights and car rentals — we bring you the very best bargains. All you’ll have to do is pick your favorite combination. After you’ve made your booking, you can add on the fun stuff like tours and experiences. Our travel packages make it easy to create an unforgettable Roundup escape.
What should I know before booking a Roundup travel package?
You’ll pick up big savings when you bundle your flights, hotels and rental cars into a package. Not just that, booking everything in one place makes trip planning much easier. So why waste time or money? Whether you’re putting together an upscale romantic escape or a budget solo adventure, check out our package deals today.
Can I choose my airline with a Roundup Expedia vacation package?
Yes — and it’s simple too. Expedia has access to more than 550 partner airlines globally. Our vacation packages give you the flexibility to pick from available flight, hotel or activity options that suit you.
If I'm not able to travel, can I cancel my Roundup vacation package?
Whether it’s your flight or hotel, you can cancel or change it. Locked in your Roundup vacation package in the last 24 hours? You may be able to make changes or cancellations for free. For bookings made more than 24 hours ago, you may incur a charge from your hotel, airline or car rental company. For more details, head to our Customer Service Portal. We’re here to help you every step of the way.

Discover the most popular places to visit in Roundup

Image for Pine Ridge Golf Club

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.

Pine Ridge Golf Club
Image for Roundup City Park

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.

Roundup City Park
Image for Musselshell Valley Historical Museum

Musselshell Valley Historical Museum

You can browse the exhibits at Musselshell Valley Historical Museum, a museum with a storied past, during your trip to Roundup. Amble around the area's parks or experience its museums.

Musselshell Valley Historical Museum

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