Title: Middlebury Vacation Packages & Trips 2026 from CA $551 | 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. ![Quality Suites Stratford](https://images.trvl-media.com/lodging/2000000/1770000/1764400/1764336/ded227e6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Quality Suites Stratford CA $551 per person Apr 24 - Apr 26 found 1 day ago Roundtrip flight included Montreal (YUL) to New Haven (HVN) 8/10 Very Good! (1,000 reviews) In the middle of a neighborhood so no close restaurants or amenities Reviewed on Mar 16, 2026 ## 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 $157 CA $180 total Apr 5 - Apr 6 includes taxes & fees 9/10 Wonderful! (2,051 reviews) close to restaurants and Yale Reviewed on Mar 23, 2026 [](https://expedia.ca/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%2F2026&selected=36721&PinnedHotelID=36721&HadPinnedHotel=true®ionId=183065) ![Hyatt Place Milford / New Haven](https://images.trvl-media.com/lodging/2000000/1570000/1562800/1562702/80833193_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hyatt Place Milford / New Haven 190 Old Gate Lane Milford CT CA $139 CA $160 total Apr 5 - Apr 6 includes taxes & fees 8.6/10 Excellent! (1,280 reviews) The best part of the stay was the breakfast. They use real eggs, not that powdered stuff. My only complaint with this property was the bed. It was terrible. The mattress was lumpy and the frame was very noisy. We stayed three nights. By the last morning, my back was so sore. Two nights would be my ... Reviewed on Mar 24, 2026 [](https://expedia.ca/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%2F2026&selected=1562702&PinnedHotelID=1562702&HadPinnedHotel=true®ionId=183065) ![Holiday Inn Express Southington by IHG](https://images.trvl-media.com/lodging/1000000/10000/4000/3929/06fc08bd_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Holiday Inn Express Southington by IHG 120 Laning St Southington CT Fully refundable CA $141 CA $163 total Apr 24 - Apr 25 includes taxes & fees 8.6/10 Excellent! (1,249 reviews) Thank you A really nice time Reviewed on Mar 24, 2026 [](https://expedia.ca/Hotel-Search?startDate=24%2F04%2F2026&endDate=25%2F04%2F2026&selected=3929&PinnedHotelID=3929&HadPinnedHotel=true®ionId=183065) [See all 1,054 properties in Middlebury](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=26%2F03%2F2026&endDate=27%2F03%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