Title: Book the Best South Side LUXURY Hotels - Upscale Hotels in South Side, Billings | Expedia.ca [Vacation Rentals in Billings](https://expedia.ca/Billings-Vacation-Rentals.d583.Travel-Guide-VacationRentals)[Flights to Billings](https://expedia.ca/Cheap-Flights-To-Billings.d583.Travel-Guide-Flights)[South Side Car Rentals](https://expedia.ca/Car-Rentals-In-South-Side.d553248635976470230.Car-Rental-Guide)[South Side Vacations](https://expedia.ca/South-Side.d553248635976470230.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/luxury.jpeg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Luxury Hotels in South Side, Billings ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](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) ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on South Side Luxury Hotels Tonight [Oct 13 - Oct 14](https://www.expedia.ca/Hotel-Search?regionId=553248635976470230&startDate=2025-10-13&endDate=2025-10-14&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=553248635976470230&startDate=2025-10-14&endDate=2025-10-15&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976470230&startDate=2025-10-17&endDate=2025-10-19&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976470230&startDate=2025-10-24&endDate=2025-10-26&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top South Side Luxury Hotels ## Top South Side Hotel Reviews ![Ledgestone Suites Hotel Billings](//images.trvl-media.com/lodging/8000000/7120000/7110900/7110813/b8f324a0_y.jpg) ### Ledgestone Suites Hotel Billings 10/10 Excellent "Very clean and very spacious room! Staff is extremely friendly and fast checkin. Loved it!" [](https://expedia.ca/Billings-Hotels-Ledgestone-Hotel-Billings.h7110813.Hotel-Information) ![Days Inn by Wyndham Billings](//images.trvl-media.com/lodging/1000000/30000/26200/26129/4c9b0ccf_y.jpg) ### Days Inn by Wyndham Billings 10/10 Excellent "Great staff!" [](https://expedia.ca/Billings-Hotels-Days-Inn-By-Wyndham-Billings.h26129.Hotel-Information) ![Best Western Plus Clocktower Inn](//images.trvl-media.com/lodging/1000000/30000/26500/26437/5f852833_y.jpg) ### Best Western Plus Clocktower Inn 10/10 Excellent "Great hotel. Breakfast at Stella’s was wonderful and convenient. Everything is in walking distance downtown; wonderful restaurants and breweries. " [](https://expedia.ca/Billings-Hotels-Best-Western-Plus-Clocktower-Inn.h26437.Hotel-Information) ![Boothill Inn And Suites](//images.trvl-media.com/lodging/1000000/890000/889800/889709/cf5bd445_y.jpg) ### Boothill Inn And Suites 10/10 Excellent "Great place to stay!" [](https://expedia.ca/Billings-Hotels-Boothill-Inn-And-Suites.h889709.Hotel-Information) ![Hilltop Inn by Riversage](//images.trvl-media.com/lodging/1000000/200000/199900/199849/6adf0770_y.jpg) ### Hilltop Inn by Riversage 10/10 Excellent "The whole 1st floor has major water damage. It smell moldy" [](https://expedia.ca/Billings-Hotels-Hilltop-Inn-By-Riversage.h199849.Hotel-Information) ![Dude Rancher Lodge](//images.trvl-media.com/lodging/1000000/40000/37900/37816/a1e00578_y.jpg) ### Dude Rancher Lodge 10/10 Excellent "This is older (on historical list), but quaint and clean. Love the fireplace and gathering area, breakfast was in a separate dining room. We had the usual in-room amenities, and the front desk gals were really nice. You can walk to a number of restaurants, brew pub, etc, and the new, modern library is almost next door. We would stay again!" [](https://expedia.ca/Billings-Hotels-Dude-Rancher-Lodge.h37816.Hotel-Information) ![SureStay Plus Hotel by Best Western Billings](//images.trvl-media.com/lodging/2000000/1610000/1608200/1608129/0d9e66b8_y.jpg) ### SureStay Plus Hotel by Best Western Billings 10/10 Excellent "All great" [](https://expedia.ca/Billings-Hotels-SureStay-Plus-Hotel-By-Best-Western-Billings.h1608129.Hotel-Information) ![Super 8 by Wyndham Billings](//images.trvl-media.com/lodging/1000000/460000/459600/459516/db35e6b1_y.jpg) ### Super 8 by Wyndham Billings 10/10 Excellent "Great stay. Staff was excellent. Older property in need of upgrades, but very clean and safe." [](https://expedia.ca/Billings-Hotels-Super-8-By-Wyndham-Billings.h459516.Hotel-Information) ![Billings Hotel and Convention Center](//images.trvl-media.com/lodging/1000000/30000/28000/27953/1745d3d6_y.jpg) ### Billings Hotel and Convention Center 10/10 Excellent "Friendly staff and clean room " [](https://expedia.ca/Billings-Hotels-Billings-Hotel-And-Convention-Center.h27953.Hotel-Information) ## Frequently asked questions ### Are you searching for a great accommodation for your luxury trip to South Side? > Use Expedia and let us help you arrange a flight to Billings Logan Intl. Airport (BIL) airport, and then select from different places to stay that will deliver the luxury you want. Amenities are an important consideration when you plan a trip, so we make it easy to get what you'd like to make your stay special. If you want a posh hotel with fine dining, a spa, or several swimming pools, Expedia can assist you in finding the best luxury hotel experience that South Side offers. South Side has some interesting things to see and do including Billings Depot and Western Heritage Center, so you might want to take in the local sights during your visit. ### What's there to see and do in South Side? > Enjoy all that South Side has to offer and visit Billings Depot, Skypoint, and The Pub Station. If you have a little extra time during your trip, you might want to check out Alberta Bair Theater and Moss Mansion Museum. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [4 Star Hotels in Billings](https://www.expedia.ca/4Star-Billings-Hotels.s40-0-d583.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Billings](https://www.expedia.ca/5Star-Billings-Hotels.s50-0-d583.Travel-Guide-Filter-Hotels) - [Hotels near Alberta Bair Theater](https://www.expedia.ca/Alberta-Bair-Theater-Hotels.0-l6115412-0.Travel-Guide-Filter-Hotels) - [Farmstay in Billings](https://www.expedia.ca/Billings-Agritourism.d583-aaAgritourism.Travel-Guide-Accommodation) - [Aparthotels in Billings](https://www.expedia.ca/Billings-Apart-Hotels.d583-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Billings](https://www.expedia.ca/Billings-Bed-And-Breakfast.d583-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cabin Rentals in Billings](https://www.expedia.ca/Billings-Cabins.d583-aaCabins.Travel-Guide-Accommodation) - 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