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.
Northern Hotel
Downtown Billings
Price was CA $1,444, price is now CA $1,219 per person
CA $1,219
per person
Jun 22 - Jun 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Billings (BIL)
9.6/10 Exceptional! (1,197 reviews)
Valet is very much appreciated! Rooms are clean, quiet! Staff very nice and helpful. Would be nice to have clearer information on room rates. Would stay again.
Reviewed on Apr 8, 2026
Ledgestone Suites Hotel Billings
Price was CA $1,137, price is now CA $1,051 per person
CA $1,051
per person
Jun 22 - Jun 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Billings (BIL)
9.4/10 Exceptional! (1,440 reviews)
Parking was easy. Kitchen had everything. Gym was amazing. Beds were comfortable. Very clean and wll mantinanced. Got our deposit hold quickly! We will be back here again next month!
Reviewed on Apr 13, 2026
Super 8 by Wyndham Billings
Price was CA $1,072, price is now CA $1,019 per person
CA $1,019
per person
Jun 22 - Jun 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Billings (BIL)
8/10 Very Good! (1,583 reviews)
The room was clean and bed was vert comfortable.
Reviewed on Apr 11, 2026
Country Inn & Suites by Radisson, Billings, MT
Price was CA $1,215, price is now CA $1,158 per person
CA $1,158
per person
Jun 22 - Jun 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Billings (BIL)
8.4/10 Very Good! (1,002 reviews)
Nice rooms Nice people, Beds are soft, pillows were soft. Everything was nice and clean. But, request a room on the back side of the hotel. The road noise is loud on the front. We will be staying here again. Super convenient to the airport!
Reviewed on Apr 9, 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 Apr 27 to Apr 28
CA $93
CA $101 total
Apr 27 - Apr 28
includes taxes & fees
8.4/10 Very Good! (151 reviews)
Wonderful staff and good food
Reviewed on Apr 12, 2026
Montana Country Retreat w/ Hot Tub-Near Lewistown
Grass Range MT
10/10 Exceptional! (1 review)
Easy check in process! We loved the fenced backyard for our dogs.
Reviewed on Mar 30, 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.
