Roundup Vacation Packages
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Your Roundup Vacation
Well known for its small-town feel and friendly locals, Roundup is an excellent getaway destination. Book one of our Roundup vacation packages and discover all that this exciting city has to offer. If taking in sights is on the cards during your trip to Roundup, swing by major attractions like Musselshell Valley Historical Museum, Roundup City Park and Pine Ridge Golf Club. Expedia has what you need to escape your daily routine. Tailor your vacation to Roundup to match your travel style, whatever that may be!
Top Roundup Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Billings Hotel and Convention Center
Southwest Corridor
Price was CA $1,869, price is now CA $1,157 per person
CA $1,157
per person
Jul 1 - Jul 7
found 17 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Billings (BIL)
8.2/10 Very Good! (1,558 reviews)
We stay here anytime we visit Billings. Affordable, clean and great amenities.
Reviewed on May 23, 2026
Northern Hotel
Downtown Billings
Price was CA $1,895, price is now CA $1,496 per person
CA $1,496
per person
Jul 1 - Jul 7
found 17 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Billings (BIL)
9.6/10 Exceptional! (1,222 reviews)
Everyone was helpful. It was a great location
Reviewed on May 22, 2026
Home2 Suites by Hilton Billings
Downtown Billings
Price was CA $1,837, price is now CA $1,530 per person
CA $1,530
per person
Jul 1 - Jul 7
found 17 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Billings (BIL)
9.4/10 Exceptional! (628 reviews)
A little bit of a sketchy area, as we pulled up we had people yelling and seemed to be doing illegal substances. On the other side of the parking lot a dude was getting wasted and then the cops showed up and arrested him. Our toliet clogged and we were handed a plunger to fix it ourselves. This was one of my only options in our route that was pet friendly but it was not worth what we paid. Breakfast was decent nothing fancy and the pool was good enough for my kids to get energy out.
Reviewed on May 12, 2026
Roundup Hotel Deals
Autumn's Inn
630 Main Street Roundup MT
Fully refundableReserve now, pay when you stay
The price is CA $93 per night from May 26 to May 27
CA $93
CA $101 total
May 26 - May 27
includes taxes & fees
8.4/10 Very Good! (157 reviews)
"The guy checking us in was super rude. The hotel was so dirty. Very gross"
Reviewed on May 11, 2026
Montana Country Retreat w/ Hot Tub-Near Lewistown
Grass Range MT
10/10 Exceptional! (3 reviews)
"Great fenced yard, clean, and beautiful setting. Hot tub was amazing!"
Reviewed on May 15, 2026
See the stars from this cozy guest cabin 30 minutes from Billings.
Shepherd MT
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
