Title: Roundup Vacation Rentals from $173: Search Short-Term Rentals | Expedia.com [Roundup Travel Guide](https://expedia.com/Roundup.dx183525)[Hotels in Roundup](https://expedia.com/Roundup-Hotels.d183525.Travel-Guide-Hotels)[Flights to Roundup](https://expedia.com/Cheap-Flights-To-Roundup.d183525.Travel-Guide-Flights)[Car Rentals in Roundup](https://expedia.com/Car-Rentals-In-Roundup.d183525.Car-Rental-Guide)[Roundup Vacation Packages](https://expedia.com/Roundup.d183525.Destination-Travel-Guides) ![Wild hors roundup in Montana](https://images.trvl-media.com/place/183525/c983272d-0c54-40e5-b52c-1270ce54ed65.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/183525/c983272d-0c54-40e5-b52c-1270ce54ed65.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates In two weeks [Mar 20 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=183525&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 1 - May 3](https://www.expedia.com/Hotel-Search?regionId=183525&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=183525&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jun 26 - Jun 28](https://www.expedia.com/Hotel-Search?regionId=183525&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=VR_SPRING_PROMO_183525) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.com/Hotel-Search?destination=Roundup%2C+Montana%2C+United+States+of+America®ionId=183525&latLong=46.449644%2C-108.539886&adults=2&startDate=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=CABIN) Cottages [](https://www.expedia.com/Hotel-Search?destination=Roundup%2C+Montana%2C+United+States+of+America®ionId=183525&latLong=46.449644%2C-108.539886&adults=2&startDate=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=COTTAGE) Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Roundup%2C+Montana%2C+United+States+of+America®ionId=183525&latLong=46.449644%2C-108.539886&adults=2&startDate=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=VACATION_HOME) Apartments [](https://www.expedia.com/Hotel-Search?destination=Roundup%2C+Montana%2C+United+States+of+America®ionId=183525&latLong=46.449644%2C-108.539886&adults=2&startDate=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=APARTMENT) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FRoundup-Vacation-Rentals.d183525.Travel-Guide-VacationRentals)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FRoundup-Vacation-Rentals.d183525.Travel-Guide-VacationRentals) ## Top Roundup Hotel Reviews ![Autumn's Inn](https://images.trvl-media.com/lodging/1000000/890000/889700/889698/55387a99_y.jpg) ### Autumn's Inn 10/10 Excellent "Clean and quiet. " [](https://expedia.com/Roundup-Hotels-Autumns-Inn.h889698.Hotel-Information) ![Small Town Big Sky](https://images.trvl-media.com/lodging/69000000/68760000/68759400/68759304/0c664fde_y.jpg) ### Small Town Big Sky 10/10 Excellent "Have stayed here twice highly recommend if you can find it available always booked and for good reason. Great place " [](https://expedia.com/Bouvet-Island-Hotels-Small-Town-Big-Sky.h68759304.Hotel-Information) ![Countryside 1-bedroom apartment in fabulous Billings with WiFi, AC](https://images.trvl-media.com/lodging/116000000/115060000/115051900/115051856/w1290h1935x0y15-d6375d02_y.jpg) ### Countryside 1-bedroom apartment in fabulous Billings with WiFi, AC 10/10 Excellent "Great place had everything I needed! Easy to communicate with and would definitely recommend to anyone coming to Billings! Will stay here again if I have a chance." [](https://expedia.com/Billings-Hotels-Countryside-1-Bedroom-Apartment-In-Fabulous-Billings-With-WiFi.h115051856.Hotel-Information) ![Quiet Country Burnt Cross Cabin close to Billings](https://images.trvl-media.com/lodging/69000000/68070000/68066400/68066361/fd13c242_y.jpg) ### Quiet Country Burnt Cross Cabin close to Billings 10/10 Excellent "Absolutely darling place that had everything I needed for my stay. The house was clean and the bed was very comfortable. The host was very nice and helpful and easy to get ahold of. Would highly recommend staying here!" [](https://expedia.com/Worden-Hotels-Quiet-Country-Burnt-Cross-Cabin-Close-To-Billings.h68066361.Hotel-Information) ## Find out more about Roundup **Everything you need to know about Roundup vacation rentals** Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Roundup vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on. There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Roundup vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. **Roundup vacation rentals: An excellent choice for every season** Whenever you want to travel, a warm welcome awaits you in Roundup. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Roundup in high season. Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $173 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals! **How to find incredible deals on Roundup rentals** At Expedia, we put the best Roundup vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. To find some top Roundup rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Roundup vacation. If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Roundup. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. ## Explore a world of travel with Expedia - Trending destinations on Expedia.com - All accommodation types in Roundup ### Trending destinations on Expedia.com - [Destin Vacation Rentals ](https://www.expedia.com/Destin-Vacation-Rentals.d6906.Travel-Guide-VacationRentals) - [Panama City Vacation Rentals ](https://www.expedia.com/Panama-City-Beach-Vacation-Rentals.d8021.Travel-Guide-VacationRentals) - [Hilton Head Vacation Rentals ](https://www.expedia.com/Hilton-Head-Island-Vacation-Rentals.d601684.Travel-Guide-VacationRentals) - [Gulf Shores Vacation Rentals ](https://www.expedia.com/Gulf-Shores-Vacation-Rentals.d603078.Travel-Guide-VacationRentals) - [Key West Vacation Rentals ](https://www.expedia.com/Key-West-Vacation-Rentals.d1187.Travel-Guide-VacationRentals) - [Gatlinburg Vacation Rentals ](https://www.expedia.com/Gatlinburg-Vacation-Rentals.d7474.Travel-Guide-VacationRentals) - [Maui Vacation Rentals ](https://www.expedia.com/Maui-Vacation-Rentals.d180073.Travel-Guide-VacationRentals) - [Orlando Vacation Rentals ](https://www.expedia.com/Orlando-Vacation-Rentals.d178294.Travel-Guide-VacationRentals) - [Myrtle Beach Vacation Rentals ](https://www.expedia.com/Myrtle-Beach-Vacation-Rentals.d601685.Travel-Guide-VacationRentals) - [Orange Beach Vacation Rentals ](https://www.expedia.com/Orange-Beach-Vacation-Rentals.d9136.Travel-Guide-VacationRentals) - [Pigeon Forge Vacation Rentals ](https://www.expedia.com/Pigeon-Forge-Vacation-Rentals.d8264.Travel-Guide-VacationRentals) - [Ocean City Vacation Rentals ](https://www.expedia.com/Ocean-City-Vacation-Rentals.d9151.Travel-Guide-VacationRentals) - [Outer Banks Vacation Rentals ](https://www.expedia.com/Outer-Banks-Vacation-Rentals.d602135.Travel-Guide-VacationRentals) - [San Diego Vacation Rentals ](https://www.expedia.com/San-Diego-Vacation-Rentals.d3073.Travel-Guide-VacationRentals) - [Siesta Key Vacation Rentals ](https://www.expedia.com/Siesta-Key-Vacation-Rentals.d6881.Travel-Guide-VacationRentals) - [Galveston Vacation Rentals ](https://www.expedia.com/Galveston-Vacation-Rentals.d1341.Travel-Guide-VacationRentals) - [Clearwater Beach Vacation Rentals ](https://www.expedia.com/Clearwater-Beach-Vacation-Rentals.d10759.Travel-Guide-VacationRentals) - [Palm Springs Vacation Rentals ](https://www.expedia.com/Palm-Springs-Vacation-Rentals.d180676.Travel-Guide-VacationRentals) - [Florida Keys Vacation Rentals ](https://www.expedia.com/Florida-Keys-Vacation-Rentals.d6023765.Travel-Guide-VacationRentals) - [Lake Tahoe Vacation Rentals ](https://www.expedia.com/South-Lake-Tahoe-Vacation-Rentals.d10150.Travel-Guide-VacationRentals) - [Lake of the Ozarks Vacation Rentals ](https://www.expedia.com/Lake-Ozark-Vacation-Rentals.d177772.Travel-Guide-VacationRentals) - [Florida Vacation Rentals ](https://www.expedia.com/Destinations-In-Florida.d211.Vacation-Rental-Destinations) - [Hawaii Vacation Rentals ](https://www.expedia.com/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations) - [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations) - [Vacation Homes in Roundup ](https://expedia.com/Roundup-Private-Vacation-Homes.d183525-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Cottages in Roundup ](https://expedia.com/Roundup-Cottages.d183525-aaCottages.Travel-Guide-Accommodation) - [Apartments in Roundup ](https://expedia.com/Roundup-Apartments.d183525-aaApartments.Travel-Guide-Accommodation) - [Cabin Rentals in Roundup ](https://expedia.com/Roundup-Cabins.d183525-aaCabins.Travel-Guide-Accommodation) - [Motels in Roundup ](https://expedia.com/Roundup-Motels.d183525-aaMotels.Travel-Guide-Accommodation) ## Frequently asked questions ### Can I find a vacation rental in Roundup? 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