Title: Bennington Vacation Packages & Trips 2025/2026 from CA $1,566 | Expedia.ca [Hotels in Bennington](https://expedia.ca/Bennington-Hotels.d6057349.Travel-Guide-Hotels)[Vacation Rentals in Bennington](https://expedia.ca/Bennington-Vacation-Rentals.d6057349.Travel-Guide-VacationRentals)[Flights to Bennington](https://expedia.ca/Cheap-Flights-To-Bennington.d6057349.Travel-Guide-Flights)[Things to do in Bennington](https://expedia.ca/Things-To-Do-In-Bennington.d6057349.Travel-Guide-Activities)[Bennington Car Rentals](https://expedia.ca/Car-Rentals-In-Bennington.d6057349.Car-Rental-Guide) ![](https://images.trvl-media.com/place/6057349/ddd79da6-d04a-4703-8452-12989539524e.jpg?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 #### Your Bennington Vacation Our vacation packages to Bennington allow you to create your own adventure. Tailor your getaway to your interests and needs and make every moment count in this interesting city. Every trip to Bennington needs a well-planned itinerary. Fill yours with famous sights like [Bennington College](https://www.expedia.ca/Bennington-College-North-Bennington.d6330089.Vacation-Attraction), [Hemmings Motor News Car Lovers Convenience Store & Vehicle Display](https://www.expedia.ca/Hemmings-Motor-News-Car-Lovers-Convenience-Store-Vehicle-Display-Bennington.d553248621533116692.Vacation-Attraction) and [Bennington Battle Monument](https://www.expedia.ca/Bennington-Battle-Monument-Bennington.d6115862.Vacation-Attraction). Don't put off visiting this city any longer. The ultimate Bennington vacation is only a few clicks away with Expedia. ## Top Bennington Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Relax in Style at Historic Modern on Main With Modern Amenities & Wooded Views](https://images.trvl-media.com/lodging/117000000/116550000/116547700/116547694/eef0ce00_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Relax in Style at Historic Modern on Main With Modern Amenities & Wooded Views CA $1,566 per person Nov 6 - Nov 12 found 1 day ago Roundtrip flight included Toronto (YYZ) to Albany (ALB) No reviews [](https://expedia.ca/go/package/search/FlightHotel/2025-11-06/2025-11-12/?FromAirport=YYZ&Destination=ALB&NumRoom=1&NumAdult=2&NumChild=0&hotelId=116547694&paandie=true&dealMarker=jHT3N1Ek5bIKLpyRMc9UkWd_ES28PxrIQAaiEb38CsfnjOxeLknrIWu2je46yGqN) ![Kingston Carriage House](https://images.trvl-media.com/lodging/108000000/107170000/107162400/107162350/de9b0cd3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Kingston Carriage House Roundout CA $1,676 per person Nov 6 - Nov 12 found 1 day ago Roundtrip flight included Toronto (YYZ) to Albany (ALB) 9.2/10 Wonderful! (24 reviews) I liked the record player and the room was clean and comfy. Coffee and pastries were waiting by the door in the morning. Checking in, the battery was dead in the room lock. Had to wait 30 mins for service to arrive. The shower floor was dangerously slippery! An accident waiting to happen. Was unable to connect to Wi-Fi after multiple tries. Reviewed on Aug 3, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-06/2025-11-12/?FromAirport=YYZ&Destination=ALB&NumRoom=1&NumAdult=2&NumChild=0&hotelId=107162350&paandie=true&dealMarker=jHT3N1Ek5bIKLpyRMc9UkWd_ES28PxrIQAaiEb38Csf30GefsmlWNdTbK_BVrWUg) ![Hasbrouck House](https://images.trvl-media.com/lodging/90000000/89670000/89666900/89666885/e87d8720_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hasbrouck House CA $2,217 per person Nov 6 - Nov 12 found 1 day ago Roundtrip flight included Toronto (YYZ) to Albany (ALB) 9/10 Wonderful! (49 reviews) To put my reactions in context, we were at HH for just one night that was unseasonably cold and rainy, so could not take advantage of the resort's amenities. BUT . . .we had reserved what turned out to be a 3d floor room up two flights of very narrow stairs. No one offered help with luggage. A night table lamp was missing a bulb, which we brought to staff's attention, but no replacement was brought up. The room itself was tiny. The online photo shows it with a small desk and reading chair. The room actually had neither, and I felt at some risk for hitting my head on the ceiling. All in all, it just wasn't worth what we paid for it. Reviewed on Aug 26, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-06/2025-11-12/?FromAirport=YYZ&Destination=ALB&NumRoom=1&NumAdult=2&NumChild=0&hotelId=89666885&paandie=true&dealMarker=jHT3N1Ek5bIKLpyRMc9UkR2-UkWsok5nujxDkOEaJh9hVG-QiXlv_xXcuRmNHW6G) ![The Hideout Catskills Cottage](https://images.trvl-media.com/lodging/112000000/111840000/111838100/111838036/7850b274_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Hideout Catskills Cottage CA $1,696 per person Nov 6 - Nov 12 found 1 day ago Roundtrip flight included Toronto (YYZ) to Albany (ALB) No reviews [](https://expedia.ca/go/package/search/FlightHotel/2025-11-06/2025-11-12/?FromAirport=YYZ&Destination=ALB&NumRoom=1&NumAdult=2&NumChild=0&hotelId=111838036&paandie=true&dealMarker=jHT3N1Ek5bIKLpyRMc9UkWd_ES28PxrIQAaiEb38CsfS8KwEDGu0GzqA5wky969W) ![Saratoga Lakeside Retreat](https://images.trvl-media.com/lodging/108000000/108000000/107998800/107998799/50db3fd5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Saratoga Lakeside Retreat CA $2,473 per person Nov 17 - Nov 20 found 12 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Albany (ALB) 10/10 Exceptional! (1 review) [](https://expedia.ca/go/package/search/FlightHotel/2025-11-17/2025-11-20/?FromAirport=YYZ&Destination=ALB&NumRoom=1&NumAdult=2&NumChild=0&hotelId=107998799&paandie=true&dealMarker=RNUtusT_53FWpfHsM_TBG1SmyK62FdU7ZvfxM8kWvkeCN_naBEUB-vsZZLT1fWJf) ## Ready to book your vacation to Bennington? Choose your dates ## Bennington Hotel Deals ![Best Western Bennington](https://images.trvl-media.com/lodging/1000000/20000/16400/16323/5ad1b90e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Best Western Bennington 220 Northside Drive, Bennington, VT Fully refundableReserve now, pay when you stay CA $162 CA $177 total Sep 28 - Sep 29 includes taxes & fees 7.6/10 Good! (914 reviews) "The one ice machine on the property was broken, laundry was closed down, but our room was nice, staff friendly and helpful, and breakfast was good." Reviewed on Sep 19, 2025 [](https://expedia.ca/Hotel-Search?startDate=28%2F09%2F2025&endDate=29%2F09%2F2025&selected=16323&PinnedHotelID=16323&HadPinnedHotel=true®ionId=6057349) ![Hotel Vervana, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/3000000/2580000/2577700/2577695/b33626c2_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel Vervana, Trademark Collection by Wyndham 141 West Main Street, Bennington, VT Fully refundableReserve now, pay when you stay CA $163 CA $178 total Sep 28 - Sep 29 includes taxes & fees 8.2/10 Very Good! (1,004 reviews) "Excellent stary for two days. Very nice that the room came with outdoor space." Reviewed on Sep 6, 2025 [](https://expedia.ca/Hotel-Search?startDate=28%2F09%2F2025&endDate=29%2F09%2F2025&selected=2577695&PinnedHotelID=2577695&HadPinnedHotel=true®ionId=6057349) ![The Autumn Inn](https://images.trvl-media.com/lodging/3000000/2390000/2381300/2381247/be4d3e05_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Autumn Inn 924 East Main Street, Bennington, VT Fully refundableReserve now, pay when you stay CA $110 CA $120 total Oct 5 - Oct 6 includes taxes & fees 7.6/10 Good! (610 reviews) "The staff was especially friendly and helpful. Everything was clean and well maintained." Reviewed on Sep 14, 2025 [](https://expedia.ca/Hotel-Search?startDate=05%2F10%2F2025&endDate=06%2F10%2F2025&selected=2381247&PinnedHotelID=2381247&HadPinnedHotel=true®ionId=6057349) [See all 746 properties in Bennington](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=21%2F09%2F2025&endDate=22%2F09%2F2025®ionId=6057349) 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) ### What to do in Bennington ![Vermont RT 100 Self Guided Driving Audio Tour](https://mediaim.expedia.com/localexpert/48988132/e3d55161-4da6-4678-970d-7686d5f338fa.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Vermont RT 100 Self Guided Driving Audio Tour CA $23 per traveller [](https://expedia.ca/things-to-do/vermont-rt-100-self-guided-driving-audio-tour.a48988132.activity-details) [See all activities in Bennington](https://expedia.ca/things-to-do/search?rid=6057349) ## 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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)