Title: Winston Vacation Packages & Trips 2026 from CA $774 | Expedia.ca [Hotels in Winston](https://expedia.ca/Winston-Hotels.d553248634983144235.Travel-Guide-Hotels)[Vacation Rentals in Winston](https://expedia.ca/Winston-Vacation-Rentals.d553248634983144235.Travel-Guide-VacationRentals)[Winston Car Rentals](https://expedia.ca/Car-Rentals-In-Winston.d553248634983144235.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) # Winston 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 ## Top Winston Vacation Deals Price found within the past 48 hours. Click for updated prices. ![HELENA INN AIRPORT](https://images.trvl-media.com/lodging/2000000/1280000/1276100/1276025/a508212c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### HELENA INN AIRPORT CA $774 per person Apr 26 - Apr 30 found 23 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Helena (HLN) 6.8/10 (886 reviews) Hotel needs updating. Damage on the walls and ceilings. At check in the staff was considerate, told me that there is no breakfast, and that the television channels are limited. I received a random phone call at 1:30am and again at 5am. The price is very affordable. Reviewed on Jan 26, 2026 ![Fairfield by Marriott Inn & Suites Helena North](https://images.trvl-media.com/lodging/1000000/800000/790900/790807/85a62e57_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Fairfield by Marriott Inn & Suites Helena North CA $1,094 per person Apr 9 - Apr 16 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Helena (HLN) 8/10 Very Good! (114 reviews) Great staff and clean rooms Reviewed on Feb 13, 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_553248634983144235) ## Ready to book your vacation to Winston? Choose your dates ## Winston Hotel Deals ![Days Inn by Wyndham Helena](https://images.trvl-media.com/lodging/1000000/30000/21600/21508/adb73f63_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Days Inn by Wyndham Helena 2001 Prospect Ave Helena MT Fully refundableReserve now, pay when you stay CA $101 CA $119 total Feb 16 - Feb 17 includes taxes & fees 8.4/10 Very Good! (53 reviews) Room was clean. Breakfast cooked by a nice young man was amazing and fresh. He certainly delivered the goods! Reviewed on Feb 7, 2026 [](https://expedia.ca/Hotel-Search?startDate=16%2F02%2F2026&endDate=17%2F02%2F2026&selected=21508&PinnedHotelID=21508&HadPinnedHotel=true®ionId=553248634983144235) ![Home2 Suites by Hilton Helena](https://images.trvl-media.com/lodging/22000000/21600000/21599900/21599842/24904f77_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Home2 Suites by Hilton Helena 3325 N Sanders St Helena MT Fully refundableReserve now, pay when you stay CA $151 CA $166 total Feb 22 - Feb 23 includes taxes & fees 9/10 Wonderful! (765 reviews) Clean room, good breakfast Reviewed on Feb 13, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=21599842&PinnedHotelID=21599842&HadPinnedHotel=true®ionId=553248634983144235) ![La Quinta Inn & Suites by Wyndham Helena](https://images.trvl-media.com/lodging/1000000/20000/19200/19156/e6191e60_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### La Quinta Inn & Suites by Wyndham Helena 701 Washington St Helena MT Fully refundableReserve now, pay when you stay CA $87 CA $96 total Feb 17 - Feb 18 includes taxes & fees 7.4/10 Good! (1,006 reviews) Very clean Reviewed on Feb 6, 2026 [](https://expedia.ca/Hotel-Search?startDate=17%2F02%2F2026&endDate=18%2F02%2F2026&selected=19156&PinnedHotelID=19156&HadPinnedHotel=true®ionId=553248634983144235) [See all 208 properties in Winston](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=16%2F02%2F2026&endDate=17%2F02%2F2026®ionId=553248634983144235) 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