Title: Roundup Vacation Packages & Trips 2026 from CA $1,820 | Expedia.ca [Hotels in Roundup](https://expedia.ca/Roundup-Hotels.d183525.Travel-Guide-Hotels)[Vacation Rentals in Roundup](https://expedia.ca/Roundup-Vacation-Rentals.d183525.Travel-Guide-VacationRentals)[Flights to Roundup](https://expedia.ca/Cheap-Flights-To-Roundup.d183525.Travel-Guide-Flights)[Roundup Car Rentals](https://expedia.ca/Car-Rentals-In-Roundup.d183525.Car-Rental-Guide) ![](https://images.trvl-media.com/place/183525/4856c25b-2bc8-481d-8774-5dae01307405.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Roundup Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place #### 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](https://www.expedia.ca/Musselshell-Valley-Historical-Museum-Roundup.d553248621579082932.Vacation-Attraction), [Roundup City Park](https://www.expedia.ca/Roundup-City-Park-Roundup.d553248621579082931.Vacation-Attraction) and [Pine Ridge Golf Club](https://www.expedia.ca/Pine-Ridge-Golf-Club-Roundup.d553248621579082933.Vacation-Attraction). 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](https://images.trvl-media.com/lodging/1000000/30000/28000/27953/48c9f963_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Billings Hotel and Convention Center CA $1,820 per person May 9 - May 16 found 10 hours ago Roundtrip flight included Cranbrook (YXC) to Billings (BIL) 8.2/10 Very Good! (1,483 reviews) A good place to stay Reviewed on Apr 5, 2026 ![Northern Hotel](https://images.trvl-media.com/lodging/1000000/10000/8000/7928/bfd76645_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Northern Hotel Downtown Billings CA $2,191 per person May 9 - May 16 found 10 hours ago Roundtrip flight included Cranbrook (YXC) to Billings (BIL) 9.6/10 Exceptional! (1,197 reviews) Great hotel to stay at! Beds were comfy, great location, loved the restaurants and the staff were so helpful!!! The only downside is that the rooms(or maybe just my room?) dont have a refrigerator. Since I was relying on my son to get around town I would have liked to have a fridge for snacks and leftovers. I would totally stay there again though! Reviewed on Apr 6, 2026 ![Big Horn Resort, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/2000000/1700000/1691200/1691126/60d9e74d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Big Horn Resort, an Ascend Collection Hotel CA $1,963 per person May 9 - May 16 found 10 hours ago Roundtrip flight included Cranbrook (YXC) to Billings (BIL) 7.4/10 Good! (1,002 reviews) There was plenty do for the kids to keep them entertain them without devices. Reviewed on Apr 5, 2026 ![Country Inn & Suites by Radisson, Billings, MT](https://images.trvl-media.com/lodging/1000000/910000/908500/908497/3414b278_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Country Inn & Suites by Radisson, Billings, MT CA $2,362 per person May 9 - May 16 found 10 hours ago Roundtrip flight included Cranbrook (YXC) to Billings (BIL) 8.4/10 Very Good! (1,002 reviews) Room smelled very bad. Reviewed on Mar 31, 2026 ![Hilltop Inn by Riversage](https://images.trvl-media.com/lodging/1000000/200000/199900/199849/bd815d57_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilltop Inn by Riversage Downtown Billings CA $1,963 per person May 9 - May 16 found 10 hours ago Roundtrip flight included Cranbrook (YXC) to Billings (BIL) 9/10 Wonderful! (1,246 reviews) Wonderful room; was updated b/c needed handicap shower. Staff was awesome!! Thank you! Reviewed on Apr 7, 2026 ## Ready to book your vacation to Roundup? Choose your dates ## Roundup Hotel Deals ![Autumn's Inn](https://images.trvl-media.com/lodging/1000000/890000/889700/889698/4861f291_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Autumn's Inn 630 Main Street Roundup MT Fully refundableReserve now, pay when you stay CA $94 CA $101 total Apr 14 - Apr 15 includes taxes & fees 8.4/10 Very Good! (150 reviews) Clean and quiet. Reviewed on Feb 20, 2026 [](https://expedia.ca/Hotel-Search?startDate=14%2F04%2F2026&endDate=15%2F04%2F2026&selected=889698&PinnedHotelID=889698&HadPinnedHotel=true®ionId=183525) ![Montana Country Retreat w/ Hot Tub-Near Lewistown](https://images.trvl-media.com/lodging/128000000/127070000/127060200/127060108/055af630_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### 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 [Get rates](https://expedia.ca/Hotel-Search?startDate=22%2F04%2F2026&endDate=23%2F04%2F2026&selected=127060108&PinnedHotelID=127060108&HadPinnedHotel=true®ionId=183525) [](https://expedia.ca/Hotel-Search?startDate=22%2F04%2F2026&endDate=23%2F04%2F2026&selected=127060108&PinnedHotelID=127060108&HadPinnedHotel=true®ionId=183525) ![See the stars from this cozy guest cabin 30 minutes from Billings.](https://images.trvl-media.com/lodging/89000000/88260000/88255700/88255682/ffa66e63_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### See the stars from this cozy guest cabin 30 minutes from Billings. Shepherd MT [Get rates](https://expedia.ca/Hotel-Search?startDate=22%2F04%2F2026&endDate=23%2F04%2F2026&selected=88255682&PinnedHotelID=88255682&HadPinnedHotel=true®ionId=183525) [](https://expedia.ca/Hotel-Search?startDate=22%2F04%2F2026&endDate=23%2F04%2F2026&selected=88255682&PinnedHotelID=88255682&HadPinnedHotel=true®ionId=183525) [See all 16 properties in Roundup](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=09%2F04%2F2026&endDate=10%2F04%2F2026®ionId=183525) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## Explore a world of travel with Expedia \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app