Title: Bennington Vacation Packages & Trips 2026 from CA $1,276 | 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/6057349/050d26ec-80e0-46da-960f-412404f2cf24.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. ![The Cornell Inn, Lenox & The Berkshires](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/63812de9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Cornell Inn, Lenox & The Berkshires CA $1,276 per person Jun 7 - Jun 12 found 7 hours ago Roundtrip flight included Calgary (YYC) to Albany (ALB) 9/10 Wonderful! (1,001 reviews) Always a pleasant experience. We stay once a year Reviewed on Apr 6, 2026 ![Sleeps 40 Heated Pool Hot Tub Fire Pit Game Room Brookside Mountain Retreat by Avantstay](https://images.trvl-media.com/lodging/126000000/125310000/125305600/125305546/53d4f091_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sleeps 40 Heated Pool Hot Tub Fire Pit Game Room Brookside Mountain Retreat by Avantstay CA $7,317 per person Jun 7 - Jun 12 found 7 hours ago Roundtrip flight included Calgary (YYC) to Albany (ALB) No reviews ![Prospect Berkshires](https://images.trvl-media.com/lodging/117000000/116740000/116739800/116739795/9aaa75ce_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Prospect Berkshires CA $1,852 per person Jun 7 - Jun 12 found 7 hours ago Roundtrip flight included Calgary (YYC) to Albany (ALB) 9.8/10 Exceptional! (23 reviews) The cabins are brand new, the property is gorgeous, restaurant features local and quality product and the staff is very responsive via text message. The lakeside sauna is private and easy to reserve. Great place! Reviewed on Feb 20, 2026 ![Secluded Estate Optional Guest House, Pond, Playroom, Gym & Theater Sunny Pond by Avantstay](https://images.trvl-media.com/lodging/105000000/104350000/104348700/104348623/e8b5f5fc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Secluded Estate Optional Guest House, Pond, Playroom, Gym & Theater Sunny Pond by Avantstay CA $7,294 per person Jun 7 - Jun 12 found 7 hours ago Roundtrip flight included Calgary (YYC) to Albany (ALB) No reviews ![Chester by Avantstay Amazing Views, Secluded Home, A True City Escape!](https://images.trvl-media.com/lodging/91000000/90940000/90931100/90931052/5aa942e0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Chester by Avantstay Amazing Views, Secluded Home, A True City Escape! CA $3,338 per person Jun 7 - Jun 12 found 7 hours ago Roundtrip flight included Calgary (YYC) to Albany (ALB) No reviews ## Ready to book your vacation to Bennington? Choose your dates ## Bennington Hotel Deals ![Hotel Vervana, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/3000000/2580000/2577700/2577695/0d5e7c05_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 $153 CA $166 total Apr 14 - Apr 15 includes taxes & fees 8.2/10 Very Good! (1,001 reviews) Our room was not cleaned properly, garbage under the bed. We were moved to a different room where the fridge was broken The third room was OK, no garbage under the bed but not swept in years. Reviewed on Apr 5, 2026 [](https://expedia.ca/Hotel-Search?startDate=14%2F04%2F2026&endDate=15%2F04%2F2026&selected=2577695&PinnedHotelID=2577695&HadPinnedHotel=true®ionId=6057349) ![Hampton Inn Bennington](https://images.trvl-media.com/lodging/2000000/1200000/1192000/1191981/7884a10e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hampton Inn Bennington 51 Hannaford Square Bennington VT Fully refundableReserve now, pay when you stay CA $185 CA $201 total Apr 26 - Apr 27 includes taxes & fees [](https://expedia.ca/Hotel-Search?startDate=26%2F04%2F2026&endDate=27%2F04%2F2026&selected=1191981&PinnedHotelID=1191981&HadPinnedHotel=true®ionId=6057349) ![Knotty Pine](https://images.trvl-media.com/lodging/120000000/119110000/119106200/119106200/3d1e6eef_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Knotty Pine 130 Northside Dr Bennington VT Fully refundableReserve now, pay when you stay CA $158 CA $172 total Apr 8 - Apr 9 includes taxes & fees 8.6/10 Excellent! (88 reviews) Cozy and Comfortable Room and Friendly Service. I am definitely reserving a room here again sometime soon! Awesome family owned business! Highly Recommend to anyone looking for a place to stay while traveling! Reviewed on Mar 12, 2026 [](https://expedia.ca/Hotel-Search?startDate=08%2F04%2F2026&endDate=09%2F04%2F2026&selected=119106200&PinnedHotelID=119106200&HadPinnedHotel=true®ionId=6057349) [See all 781 properties in Bennington](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=08%2F04%2F2026&endDate=09%2F04%2F2026®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/fc006ec3-5e60-4c71-81f0-c520c3a7c8ec.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