Title: Roundup Vacation Home Rentals : Search Top Private Vacation Homes for Rent | 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)[Roundup Vacation Packages](https://expedia.ca/Roundup.d183525.Destination-Travel-Guides) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Roundup Vacation Rentals ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=183525&startDate=2025-10-17&endDate=2025-10-19&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=183525&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=183525&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=183525&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Roundup Vacation Homes ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/69000000/68760000/68759400/68759304/0c664fde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/69000000/68760000/68759400/68759304/a0c278e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/69000000/68760000/68759400/68759304/e1c5a3fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/69000000/68760000/68759400/68759304/c767339b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Small Town Big Sky Winnett 9.4/10 Exceptional (6) "Great open kitchen and living room for a large group to hang out we all enjoyed the stay" [](https://www.expedia.ca/Bouvet-Island-Hotels-Small-Town-Big-Sky.h68759304.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/112000000/111410000/111403200/111403196/464eac5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/112000000/111410000/111403200/111403196/92b89892.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, towels](https://images.trvl-media.com/lodging/112000000/111410000/111403200/111403196/0f4ea909.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/112000000/111410000/111403200/111403196/8a6b18fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming bungalow with AC and WiFi in a private rural part of Billings. Billings [](https://www.expedia.ca/Billings-Hotels-Charming-Bungalow-With-AC-And-WiFi-In-A-Private-Rural-Part-Of-Billings.h111403196.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/112000000/111830000/111822800/111822766/3e309421_edited_6c31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/112000000/111830000/111822800/111822766/a1a81cde_edited_83dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/112000000/111830000/111822800/111822766/9786441c_edited_19c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/112000000/111830000/111822800/111822766/548a7118_edited_a48e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3 Bedroom 2 bath with space for classes and retreats Shepherd [](https://www.expedia.ca/Shepherd-Hotels-3-Bedroom-2-Bath-With-Space-For-Classes-And-Retreats.h111822766.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-15&endDate=2025-10-16®ionId=183525&adults=2&lodging=VACATION_HOME&sort=RECOMMENDED&openPlayBack=true) ![](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.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FRoundup-Private-Vacation-Homes.d183525-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FRoundup-Private-Vacation-Homes.d183525-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Roundup Hotel Reviews ![Countryside 1-bedroom apartment in fabulous Billings with WiFi, AC](//images.trvl-media.com/lodging/116000000/115060000/115051900/115051856/36dcb421_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.ca/Billings-Hotels-Countryside-1-Bedroom-Apartment-In-Fabulous-Billings-With-WiFi.h115051856.Hotel-Information) ![Autumn's Inn](//images.trvl-media.com/lodging/1000000/890000/889700/889698/55387a99_y.jpg) ### Autumn's Inn 10/10 Excellent "Staff provided excellent Montana hospitality. Room was clean comfortable and relaxing. Pizza delivered to the room was excellent. " [](https://expedia.ca/Roundup-Hotels-Autumns-Inn.h889698.Hotel-Information) ![Quiet Country Burnt Cross Cabin close to Billings](//images.trvl-media.com/lodging/69000000/68070000/68066400/68066361/8f46e89f_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.ca/Worden-Hotels-Quiet-Country-Burnt-Cross-Cabin-Close-To-Billings.h68066361.Hotel-Information) ![Small Town Big Sky](//images.trvl-media.com/lodging/69000000/68760000/68759400/68759304/0c664fde_y.jpg) ### Small Town Big Sky 10/10 Excellent "Very accommodating " [](https://expedia.ca/Bouvet-Island-Hotels-Small-Town-Big-Sky.h68759304.Hotel-Information) ![Restored Vintage Mobile Home on our small Private Ranch](//images.trvl-media.com/lodging/40000000/39090000/39084600/39084552/c003b572_y.jpg) ### Restored Vintage Mobile Home on our small Private Ranch 10/10 Excellent "Our stay was awesome!! 2nd time staying here and will definitely stay here again. " [](https://expedia.ca/Restored-Vintage-Mobile-Home-On-Our-212-Acre-Private-Ranch.h39084552.Hotel-Information) ## Find out more about Roundup ## Roundup Vacation Homes information | Number of reviews | 6 | | --- | --- | | Accommodation | 4 Vacation Homes | | Lowest Price | | | Highest Price | | ## Explore a world of travel with Expedia - Lodging - Flights - Cars - More ways to book - [Apartments in Acton](https://www.expedia.ca/Acton-Apartments.d770577855379517440-aaApartments.Travel-Guide-Accommodation) - [B&B in Acton](https://www.expedia.ca/Acton-Bed-And-Breakfast.d770577855379517440-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cheap Hotels in Acton](https://www.expedia.ca/Acton-Hotels-Cheap-Hotels.0-0-d770577855379517440-tCheapHotels.Travel-Guide-Filter-Hotels) - [Acton Hotels](https://www.expedia.ca/Acton-Hotels.d770577855379517440.Travel-Guide-Hotels) - [Motels in Acton](https://www.expedia.ca/Acton-Motels.d770577855379517440-aaMotels.Travel-Guide-Accommodation) - [Ballantine Hotels](https://www.expedia.ca/Ballantine-Hotels.d553248634983099000.Travel-Guide-Hotels) - 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