Title: Bennington Vacation Packages & Trips 2025/2026 from CA $899 | Expedia.ca [Hotels in Bennington](https://expedia.ca/Bennington-Hotels.d553248635975849202.Travel-Guide-Hotels)[Vacation Rentals in Bennington](https://expedia.ca/Bennington-Vacation-Rentals.d553248635975849202.Travel-Guide-VacationRentals)[Bennington Car Rentals](https://expedia.ca/Car-Rentals-In-Bennington.d553248635975849202.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) # Bennington 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 Bennington Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Crowne Plaza Louisville Airport Expo Ctr by IHG](https://images.trvl-media.com/lodging/1000000/20000/11400/11386/a43a56f2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Crowne Plaza Louisville Airport Expo Ctr by IHG Fairgrounds CA $899 per person Dec 20 - Dec 24 found 4 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Louisville (SDF) 8.8/10 Excellent! (874 reviews) Left a pair of hiking pants in the room. Absolutely positive the pants were left in the room, yet housekeeping claimed they couldnt find them. I doubt they even checked considering it took them 2 days to call me back. Won't stay there again. Reviewed on Nov 7, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-20/2025-12-24/?FromAirport=YYZ&Destination=SDF&NumRoom=1&NumAdult=2&NumChild=0&hotelId=11386&paandie=true&dealMarker=XHuX-2Bj7PGzFmoqrl15zWeG_m8H0wqNsgkELT-mnSjMIGYi_y7mdn7qRV55ldwA) ![Omni Louisville Hotel](https://images.trvl-media.com/lodging/22000000/21110000/21106200/21106192/4c7c479b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Omni Louisville Hotel Downtown Louisville CA $1,240 per person Dec 20 - Dec 24 found 4 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Louisville (SDF) 9.2/10 Wonderful! (1,645 reviews) Great location and amenities Reviewed on Nov 2, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-20/2025-12-24/?FromAirport=YYZ&Destination=SDF&NumRoom=1&NumAdult=2&NumChild=0&hotelId=21106192&paandie=true&dealMarker=XHuX-2Bj7PGzFmoqrl15zZRXPifwqaSta3hIyx5bIz76LeatqgLiWI6jPl7zW-Pa) ![Moxy Louisville Downtown](https://images.trvl-media.com/lodging/37000000/36890000/36884900/36884898/050ebd40_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Moxy Louisville Downtown Downtown Louisville CA $994 per person Dec 20 - Dec 24 found 4 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Louisville (SDF) 9.2/10 Wonderful! (678 reviews) Nice hotel. Cool vibe. Very clean and friendly. Walking distance to everything. Would stay again Reviewed on Oct 26, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-20/2025-12-24/?FromAirport=YYZ&Destination=SDF&NumRoom=1&NumAdult=2&NumChild=0&hotelId=36884898&paandie=true&dealMarker=XHuX-2Bj7PGzFmoqrl15zWeG_m8H0wqNsgkELT-mnShrMHduefq4QVLlhIsZTyRm) ![Galt House Hotel Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/200000/191500/191434/b5c46c3f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Galt House Hotel Trademark Collection by Wyndham Downtown Louisville CA $979 per person Dec 20 - Dec 24 found 4 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Louisville (SDF) 9/10 Wonderful! (3,693 reviews) Great experience at The Galt. Will be back. Service at Walker’s Exchange was very slow even though the restaurant was empty. Ahbijit means well and was very nice, but needs more training how to refresh drinks and check on tables. Jockey Silks was lovely and the bartender was awesome with bourbon knowledge. It was a little chilly in there though. Sizzle was our fave. Sam gave awesome service and made our evening memorable. Jeff Ruby’s meal was horrible. The two of us shared a hatchet ribeye that was way too rare and they took it back and it was almost inedible when they brought it back. Almost like it was microwaved. Yuk. Brussels sprouts were mushy. Music was great! Reviewed on Nov 5, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-20/2025-12-24/?FromAirport=YYZ&Destination=SDF&NumRoom=1&NumAdult=2&NumChild=0&hotelId=191434&paandie=true&dealMarker=XHuX-2Bj7PGzFmoqrl15zWeG_m8H0wqNsgkELT-mnShk7gDRpatnui8PwhBHqL_C) ![Homewood Suites by Hilton Louisville Downtown, KY](https://images.trvl-media.com/lodging/22000000/21600000/21599900/21599840/5c04f012_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Homewood Suites by Hilton Louisville Downtown, KY Downtown Louisville CA $978 per person Dec 20 - Dec 24 found 4 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Louisville (SDF) 9.2/10 Wonderful! (1,006 reviews) Very good hotel, staff and location. Reviewed on Nov 4, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-20/2025-12-24/?FromAirport=YYZ&Destination=SDF&NumRoom=1&NumAdult=2&NumChild=0&hotelId=21599840&paandie=true&dealMarker=XHuX-2Bj7PGzFmoqrl15zWeG_m8H0wqNsgkELT-mnShMEQdyjRBcwCxjVt4dWoQM) ## Ready to book your vacation to Bennington? Choose your dates ## Bennington Hotel Deals ![Belterra Casino Resort](https://images.trvl-media.com/lodging/2000000/1160000/1152900/1152807/04047b8f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Belterra Casino Resort 777 Belterra Drive, Florence, IN Fully refundableReserve now, pay when you stay 8.4/10 Very Good! (1,004 reviews) Room was clean and the staff was good. Reviewed on Nov 2, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=22%2F11%2F2025&endDate=23%2F11%2F2025&selected=1152807&PinnedHotelID=1152807&HadPinnedHotel=true®ionId=553248635975849202) [](https://expedia.ca/Hotel-Search?startDate=22%2F11%2F2025&endDate=23%2F11%2F2025&selected=1152807&PinnedHotelID=1152807&HadPinnedHotel=true®ionId=553248635975849202) ![Best Way Inn Madison](https://images.trvl-media.com/lodging/1000000/10000/8000/7911/bdd60431_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Best Way Inn Madison 700 Clifty Drive, Madison, IN Fully refundableReserve now, pay when you stay 6.8/10 (510 reviews) Very inexpensive and clean. Reviewed on Oct 19, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=22%2F11%2F2025&endDate=23%2F11%2F2025&selected=7911&PinnedHotelID=7911&HadPinnedHotel=true®ionId=553248635975849202) [](https://expedia.ca/Hotel-Search?startDate=22%2F11%2F2025&endDate=23%2F11%2F2025&selected=7911&PinnedHotelID=7911&HadPinnedHotel=true®ionId=553248635975849202) ![Ramada by Wyndham Sparta/At Speedway](https://images.trvl-media.com/lodging/1000000/980000/972800/972772/3310105f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Ramada by Wyndham Sparta/At Speedway 525 Dale Drive I 71 Exit 57 Sp, Sparta, KY Fully refundableReserve now, pay when you stay CA $115 CA $127 total Nov 12 - Nov 13 includes taxes & fees 7.8/10 Good! (1,019 reviews) Really nice staff Reviewed on Nov 2, 2025 [](https://expedia.ca/Hotel-Search?startDate=12%2F11%2F2025&endDate=13%2F11%2F2025&selected=972772&PinnedHotelID=972772&HadPinnedHotel=true®ionId=553248635975849202) [See all 152 properties in Bennington](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=09%2F11%2F2025&endDate=10%2F11%2F2025®ionId=553248635975849202) 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 ![QR code to download the app](data:image/png;base64,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)