Title: Middlebury Vacation Packages 2026 from $123 | 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 $123 ## 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. ![The Best Way Inn](https://images.trvl-media.com/lodging/114000000/113740000/113734200/113734172/dd1de9d5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Best Way Inn West New Haven $123 per person May 9 - May 11 found 9 hours ago Roundtrip flight included Atlanta (ATL) to New Haven (HVN) 4.6/10 (29 reviews) The staff was helpful. The room was clean. The place needs some repairs. Reviewed on Jun 13, 2025 ![Graduate by Hilton New Haven](https://images.trvl-media.com/lodging/38000000/37210000/37200100/37200005/f203cc93_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Graduate by Hilton New Haven Downtown New Haven $307 per person May 9 - May 11 found 9 hours ago Roundtrip flight included Atlanta (ATL) to New Haven (HVN) 9.2/10 Wonderful! (908 reviews) Loved everything about the hotel - great location, quaint and cozy rooms, clean, friendly staff and lots of character! Reviewed on Feb 12, 2026 ![Luxury Apartments by Hyatus at Pierpont](https://images.trvl-media.com/lodging/77000000/76890000/76889000/76888939/1add7dcb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Luxury Apartments by Hyatus at Pierpont The Hill $419 per person May 9 - May 11 found 8 hours ago Roundtrip flight included Atlanta (ATL) to New Haven (HVN) 9.4/10 Exceptional! (21 reviews) The place could have been a little cleaner I found hair in the bed and crumbs and dirt in the couch and under it as well the walls were stained and the carpet was stained in the bedroom it definitely was a big difference from the first time I stayed there Reviewed on Feb 16, 2026 ![Madison Beach Hotel](https://images.trvl-media.com/lodging/2000000/1210000/1209400/1209378/18df186b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Madison Beach Hotel Madison Center $471 per person May 9 - May 11 found 9 hours ago Roundtrip flight included Atlanta (ATL) to New Haven (HVN) 9.4/10 Exceptional! (336 reviews) beautiful room and views Reviewed on Dec 13, 2025 ![Mayflower Inn & Spa, Auberge Collection](https://images.trvl-media.com/lodging/1000000/180000/170800/170742/5296f0bf_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Mayflower Inn & Spa, Auberge Collection $2,030 per person May 9 - May 11 found 9 hours ago Roundtrip flight included Atlanta (ATL) to New Haven (HVN) 9.2/10 Wonderful! (54 reviews) The hotel is amazing but room services is not good if u want to dinner in the room not good food just snacks But other than that it’s amazing place Reviewed on Dec 30, 2025 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/2026-03-19/2026-03-26/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=BDR&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=PKG_SPRING_PROMO_183065) ### Discover the most popular places to visit in Middlebury #### Quassy Amusement Park 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 $111 nightly $128 total Feb 25 - Feb 26 Total with taxes and fees 9/10 Wonderful! (2,029 reviews) Great staff. Rooms are clean but not special. Location is spectacular. Reviewed on Feb 18, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F25%2F2026&endDate=2%2F26%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 $115 nightly $132 total Mar 22 - Mar 23 Total with taxes and fees 8.8/10 Excellent! (1,016 reviews) Very modern new clean facilities Reviewed on Feb 16, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F22%2F2026&endDate=3%2F23%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 $144 nightly $165 total Mar 1 - Mar 2 Total with taxes and fees 8.6/10 Excellent! (1,006 reviews) Doors were not soft close which meant the entire night doors are slamming shut. Couple that with the fact you can hear the people above you as well (toilets flushing). The service was incredible and the lobby is beautiful, however I would not go back due to those issues Reviewed on Feb 17, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F1%2F2026&endDate=3%2F2%2F2026&selected=49957&PinnedHotelID=49957&HadPinnedHotel=true®ionId=183065) [See all 1,047 properties in Middlebury](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F20%2F2026&endDate=2%2F21%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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