Title: Middlebury Vacation Packages 2026 from $364 | Expedia.com [Middlebury Travel Guide](https://expedia.com/Middlebury.dx183065)[Hotels in Middlebury](https://expedia.com/Middlebury-Hotels.d183065.Travel-Guide-Hotels)[Vacation Rentals in Middlebury](https://expedia.com/Middlebury-Vacation-Rentals.d183065.Travel-Guide-VacationRentals)[Flights to Middlebury](https://expedia.com/Cheap-Flights-To-Middlebury.d183065.Travel-Guide-Flights)[Car Rentals in Middlebury](https://expedia.com/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 Vacations from $364 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 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.com/Quassy-Amusement-Park-Middlebury.d6089847.Vacation-Attraction), [Palace Theatre](https://www.expedia.com/Palace-Theatre-Waterbury.d6247005.Vacation-Attraction) and [Brass Mill Center](https://www.expedia.com/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. ## The Latest Middlebury vacation packages Price found within the past 48 hours. Click for updated prices. ![Omni New Haven Hotel at Yale](https://images.trvl-media.com/lodging/1000000/50000/50000/49957/b7b5473a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Omni New Haven Hotel at Yale Downtown New Haven $364 per person May 20 - May 22 found 6 hours ago Roundtrip flight included Concord (USA) to New Haven (HVN) 8.6/10 Excellent! (1,008 reviews) Excellent, friendly staff and a large comfortable room. Reviewed on Mar 26, 2026 ![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 Save 100% on your flight $757 per person May 12 - May 14 found 5 hours ago Roundtrip flight included Fort Lauderdale (FLL) to New Haven (HVN) No reviews ![Madison Beach Hotel](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/1ec18076_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Madison Beach Hotel Madison Center Save 100% on your flight $574 per person May 20 - May 22 found 6 hours ago Roundtrip flight included Concord (USA) to New Haven (HVN) 9.4/10 Exceptional! (349 reviews) We toured the Spa but did not have an opportunity to take advantage of the services during our overnight stay. The staff was very helpful and the spa calm and inviting. Reviewed on Mar 25, 2026 ![Hyatus Luxury Residences City Crossing](https://images.trvl-media.com/lodging/77000000/76890000/76889000/76888939/2e7a06d9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatus Luxury Residences City Crossing The Hill $578 per person May 20 - May 22 found 6 hours ago Roundtrip flight included Concord (USA) to New Haven (HVN) 9.2/10 Wonderful! (30 reviews) Great stay with many amenities to enjoy within the building! Reviewed on Apr 3, 2026 Don't see what you're looking for? See all available trips from Columbus to Middlebury [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-05-04/2026-05-11/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=BDR&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ### Discover the most popular places to visit in Middlebury #### Quassy Amusement Park 4.5/5(15 reviews) Bring the kiddos to Quassy Amusement Park and have a fun-filled day at this theme park in Middlebury. Attend a sporting event in this family-friendly area. [](https://expedia.com/Quassy-Amusement-Park-Middlebury.d6089847.Vacation-Attraction) ## 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 refundableReserve now, pay when you stay $108 nightly $124 total Apr 12 - Apr 13 Total with taxes and fees 9/10 Wonderful! (2,056 reviews) The staff was outstanding! So kind and helpful. Reviewed on Apr 3, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F12%2F2026&endDate=4%2F13%2F2026&selected=36721&PinnedHotelID=36721&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 $108 nightly $124 total Apr 12 - Apr 13 Total with taxes and fees 8.6/10 Excellent! (1,255 reviews) breakfast was fine did not use a/c Reviewed on Mar 31, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F12%2F2026&endDate=4%2F13%2F2026&selected=3929&PinnedHotelID=3929&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 Fully refundableReserve now, pay when you stay $110 nightly $126 total Apr 5 - Apr 6 Total with taxes and fees 8.6/10 Excellent! (1,289 reviews) Room was very spacious and we never felt cramped. Reviewed on Apr 3, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F5%2F2026&endDate=4%2F6%2F2026&selected=1562702&PinnedHotelID=1562702&HadPinnedHotel=true®ionId=183065) [See all 1,075 properties in Middlebury](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=4%2F5%2F2026&endDate=4%2F6%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. ## Find the Best Middlebury Vacation Packages ## Middlebury Essential Information | Language | English | | --------------- | --------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | U.S dollars | | Closest Airport | Tweed - New Haven Regional Airport (HVN) | | Population | 7,000 | | Max Temp Winter | 35ºF | | Max Temp Summer | 80ºF | | Top Sights | [Quassy Amusement Park](https://www.expedia.com/Quassy-Amusement-Park-Middlebury.d6089847.Vacation-Attraction), [Palace Theatre](https://www.expedia.com/Palace-Theatre-Waterbury.d6247005.Vacation-Attraction) and [Mount Southington Ski Area](https://www.expedia.com/Mount-Southington-Ski-Area-Plantsville.d6089845.Vacation-Attraction) | ## More vacations you might like ![](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.com/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.com/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) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.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.com/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.com/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.com/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.com/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ![Gay Friendly Vacations](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ Friendly Vacations [](https://expedia.com/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ_Friendly%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2017/07/05/170615_Adventure_1320_2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adventure Vacations [](https://expedia.com/lp/theme-vacations/adventure-vacations?rfrr=editorial.Adventure_Vacations.click) ![Vacations in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.com/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/honeymoon_hawaii.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Honeymoon Vacations [](https://expedia.com/lp/theme-vacations/honeymoon-vacations?rfrr=editorial.Honeymoon_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/Mountain-vacations.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Mountain Vacations [](https://expedia.com/lp/theme-vacations/mountain-vacations?rfrr=editorial.Mountain_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/fishing-vacations-2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Fishing Vacations [](https://expedia.com/lp/theme-vacations/fishing-vacations?rfrr=editorial.Fishing_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adults Only Vacations [](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Waterpark Vacations [](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Scuba Diving Vacations [](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Yoga Vacations [](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Cheap Vacations [](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Solo Vacations [](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click) ## Frequently asked questions ### How much does a Middlebury vacation package cost? ### What are the cheapest months to go to Middlebury? ### How many days is enough for Middlebury? ### How to find the best Middlebury package deals? ### Is it cheaper to book a Middlebury vacation as a package? ### When to book a vacation package to Middlebury? ### Does Expedia offer Book Now, Pay Later Middlebury vacation packages? ## Explore a world of travel with Expedia - Lodging - Flights - 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](https://www.expedia.com/lp/flights/tri/oxc/tri-cities-to-oxford) - [Flights from Islip (ISP) to Oxford (OXC) ](https://www.expedia.com/lp/flights/isp/oxc/islip-to-oxford) - [Flights from New York (LGA) to Oxford (OXC) ](https://www.expedia.com/lp/flights/lga/oxc/new-york-to-oxford) - [Flights from Oakland (OAK) to Oxford (OXC) ](https://www.expedia.com/lp/flights/oak/oxc/oakland-to-oxford) - [Flights from Pensacola (PNS) to Oxford (OXC) ](https://www.expedia.com/lp/flights/pns/oxc/pensacola-to-oxford) - [Flights from Charleston (CRW) to Oxford (OXC) ](https://www.expedia.com/lp/flights/crw/oxc/charleston-to-oxford) - [Flights from Dakar (DSS) to Oxford (OXC) ](https://www.expedia.com/lp/flights/dss/oxc/dakar-to-oxford) - [Flights from Trenton (TTN) to Oxford (OXC) ](https://www.expedia.com/lp/flights/ttn/oxc/trenton-to-oxford) - [Flights from Manchester (MHT) to Oxford (OXC) ](https://www.expedia.com/lp/flights/mht/oxc/manchester-to-oxford) - [Flights from Elmira (ELM) to Oxford 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