Title: Middlebury Vacation Packages & Trips 2026 from CA $2,679 | Expedia.ca [Hotels in Middlebury](https://expedia.ca/Middlebury-Hotels.d183065.Travel-Guide-Hotels)[Vacation Rentals in Middlebury](https://expedia.ca/Middlebury-Vacation-Rentals.d183065.Travel-Guide-VacationRentals)[Middlebury Car Rentals](https://expedia.ca/Car-Rentals-In-Middlebury.d183065.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Middlebury 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 Middlebury Vacation You'll find plenty to like about Middlebury, from its rich history to its cultural experiences. When you're ready to say hello to this fascinating city, our Middlebury vacation packages are calling your name. A trip to Middlebury is a terrific opportunity to sightsee. Be sure to visit popular attractions like [Quassy Amusement Park](https://www.expedia.ca/Quassy-Amusement-Park-Middlebury.d6089847.Vacation-Attraction), [Palace Theatre](https://www.expedia.ca/Palace-Theatre-Waterbury.d6247005.Vacation-Attraction) and [Brass Mill Center](https://www.expedia.ca/Brass-Mill-Center-Waterbury.d6220535.Vacation-Attraction). No matter your travel plans or budget, organizing your ultimate tailored Middlebury vacation is a breeze with Expedia. ## Top Middlebury Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Beechmont - Perfect for Family Retreat!](https://images.trvl-media.com/lodging/120000000/119250000/119248500/119248411/6e17e1d7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Beechmont - Perfect for Family Retreat! North End CA $2,679 per person Apr 25 - Apr 29 found 23 hours ago Roundtrip flight included Toronto (YTO) to New Haven (HVN) No reviews ## Ready to book your vacation to Middlebury? Choose your dates ## Middlebury Hotel Deals ![New Haven Hotel](https://images.trvl-media.com/lodging/1000000/40000/36800/36721/d665dc9c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### New Haven Hotel 229 George Street New Haven CT Fully refundable CA $196 CA $226 total Feb 12 - Feb 13 includes taxes & fees 9/10 Wonderful! (2,016 reviews) Excellent desk staff. Clean and quite room. Good location. Reviewed on Feb 4, 2026 [](https://expedia.ca/Hotel-Search?startDate=12%2F02%2F2026&endDate=13%2F02%2F2026&selected=36721&PinnedHotelID=36721&HadPinnedHotel=true®ionId=183065) ![Cambria Hotel New Haven University Area](https://images.trvl-media.com/lodging/79000000/78620000/78614500/78614483/a6a28eee_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Cambria Hotel New Haven University Area 20 Dwight Street New Haven CT Fully refundable CA $142 CA $163 total Mar 8 - Mar 9 includes taxes & fees 8.6/10 Excellent! (1,006 reviews) Nice fromt desk staff. Clean & comfortable room. Reviewed on Jan 26, 2026 [](https://expedia.ca/Hotel-Search?startDate=08%2F03%2F2026&endDate=09%2F03%2F2026&selected=78614483&PinnedHotelID=78614483&HadPinnedHotel=true®ionId=183065) ![Omni New Haven Hotel at Yale](https://images.trvl-media.com/lodging/1000000/50000/50000/49957/7466af25_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Omni New Haven Hotel at Yale 155 Temple St New Haven CT Fully refundableReserve now, pay when you stay CA $208 CA $239 total Feb 8 - Feb 9 includes taxes & fees 8.4/10 Very Good! (1,004 reviews) Love the staff very nice and attentive. Very clean nice bar!!! Close to everything, I’ll definitely will stay there again!! Reviewed on Feb 6, 2026 [](https://expedia.ca/Hotel-Search?startDate=08%2F02%2F2026&endDate=09%2F02%2F2026&selected=49957&PinnedHotelID=49957&HadPinnedHotel=true®ionId=183065) [See all 1,033 properties in Middlebury](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=08%2F02%2F2026&endDate=09%2F02%2F2026®ionId=183065) 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