Title: Shepherd Vacation Packages & Trips 2026 from CA $1,154 | Expedia.ca [Hotels in Shepherd](https://expedia.ca/Shepherd-Hotels.d3000445886.Travel-Guide-Hotels)[Vacation Rentals in Shepherd](https://expedia.ca/Shepherd-Vacation-Rentals.d3000445886.Travel-Guide-VacationRentals)[Shepherd Car Rentals](https://expedia.ca/Car-Rentals-In-Shepherd.d3000445886.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Shepherd 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 Shepherd Vacation The adventure-filled city of Shepherd is calling. Discover its hot spots and hidden treasures with a Shepherd vacation package that's tailored to you. Every trip to Shepherd should include some sightseeing. [Town & Country Lanes and Lounge](https://www.expedia.ca/Town-Country-Lanes-And-Lounge-Billings.d553248621532651700.Vacation-Attraction) is a popular place to kick things off. A couple of quick clicks is all it takes to build your dream Shepherd vacation on Expedia. ## Top Shepherd Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Dude Rancher Lodge](https://images.trvl-media.com/lodging/1000000/40000/37900/37816/a1e00578_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Dude Rancher Lodge Downtown Billings CA $1,154 per person May 8 - May 11 found 17 hours ago Roundtrip flight included Regina (YQR) to Billings (BIL) 8.6/10 Excellent! (1,068 reviews) Great rustic lodge , rooms are smallish but comfortable, could use shelf space in the bathroom . Nice having the coffee shop right there . Staff is welcoming and very helpful . Will definitely stay again if in the area . Reviewed on Feb 25, 2026 ![Billings Hotel and Convention Center](https://images.trvl-media.com/lodging/1000000/30000/28000/27953/1745d3d6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Billings Hotel and Convention Center CA $1,179 per person May 8 - May 11 found 17 hours ago Roundtrip flight included Regina (YQR) to Billings (BIL) 8/10 Very Good! (1,349 reviews) Room was clean. Hot tub and pool was clean. Kinda noisy but worth the price Reviewed on Mar 1, 2026 ![Northern Hotel](https://images.trvl-media.com/lodging/1000000/10000/8000/7928/4fe8e929_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Northern Hotel Downtown Billings CA $1,336 per person May 8 - May 11 found 17 hours ago Roundtrip flight included Regina (YQR) to Billings (BIL) 9.6/10 Exceptional! (1,147 reviews) This is our favorite short-distance vacation spot. Excellent stay as always. Had a bit of a snafu with our parking garage pass, but they fixed it. Reviewed on Feb 26, 2026 ![Candlewood Suites Billings West by IHG](https://images.trvl-media.com/lodging/115000000/114740000/114736100/114736036/1b5bd40f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Candlewood Suites Billings West by IHG CA $1,290 per person May 8 - May 11 found 17 hours ago Roundtrip flight included Regina (YQR) to Billings (BIL) 9.8/10 Exceptional! (21 reviews) Very nice Staff was great Reviewed on Feb 4, 2026 ![Baymont by Wyndham Billings](https://images.trvl-media.com/lodging/1000000/20000/14400/14376/7de6e407_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Baymont by Wyndham Billings CA $1,188 per person May 8 - May 11 found 17 hours ago Roundtrip flight included Regina (YQR) to Billings (BIL) 6/10 (1,003 reviews) The chair in the room was very stained. The shower floor was discolored. It did not feel clean. The bed was comfortable and the price was good. Reviewed on Feb 3, 2026 ![](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.ca/deals?rfrr=PKG_SPRING_PROMO_3000445886) ## Ready to book your vacation to Shepherd? Choose your dates ## Shepherd Hotel Deals ![Kelly Inn Billings Montana](https://images.trvl-media.com/lodging/1000000/30000/27500/27421/667ce956_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Kelly Inn Billings Montana 5610 South Frontage Road Billings MT Fully refundableReserve now, pay when you stay CA $130 CA $146 total Mar 8 - Mar 9 includes taxes & fees 8.6/10 Excellent! (1,874 reviews) Room was very nice . Front desk clerk was unfriendly but knew his job. Reviewed on Mar 1, 2026 [](https://expedia.ca/Hotel-Search?startDate=08%2F03%2F2026&endDate=09%2F03%2F2026&selected=27421&PinnedHotelID=27421&HadPinnedHotel=true®ionId=3000445886) ![Hyatt Place Billings](https://images.trvl-media.com/lodging/113000000/112740000/112736100/112736041/ddadd226_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hyatt Place Billings 705 Henry Chapple Street Billings MT Fully refundableReserve now, pay when you stay CA $153 CA $170 total Mar 14 - Mar 15 includes taxes & fees 9.6/10 Exceptional! (396 reviews) Everything was clean and the staff was very nice Reviewed on Mar 1, 2026 [](https://expedia.ca/Hotel-Search?startDate=14%2F03%2F2026&endDate=15%2F03%2F2026&selected=112736041&PinnedHotelID=112736041&HadPinnedHotel=true®ionId=3000445886) ![Billings Hotel and Convention Center](https://images.trvl-media.com/lodging/1000000/30000/28000/27953/1745d3d6_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Billings Hotel and Convention Center 1223 Mullowney Ln Billings MT Fully refundableReserve now, pay when you stay CA $162 CA $187 total Apr 1 - Apr 2 includes taxes & fees 8.2/10 Very Good! (1,467 reviews) Room was clean. Hot tub and pool was clean. Kinda noisy but worth the price Reviewed on Mar 1, 2026 [](https://expedia.ca/Hotel-Search?startDate=01%2F04%2F2026&endDate=02%2F04%2F2026&selected=27953&PinnedHotelID=27953&HadPinnedHotel=true®ionId=3000445886) [See all 281 properties in Shepherd](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=03%2F03%2F2026&endDate=04%2F03%2F2026®ionId=3000445886) 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