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 ## 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 Surfside Hotel](https://images.trvl-media.com/lodging/91000000/90180000/90178600/90178584/44f176e7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Surfside Hotel Lordship $364 per person Apr 24 - Apr 26 found 20 hours ago Roundtrip flight included Atlanta (ATL) to New Haven (HVN) 9.4/10 Exceptional! (179 reviews) Great place, adorable and courteous staff! Reviewed on Jan 1, 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 $1,096 per person May 3 - May 6 found 1 day ago Roundtrip non-stop flight included Fort Lauderdale (FLL) to New Haven (HVN) No reviews ![Home2 Suites by Hilton East Haven New Haven](https://images.trvl-media.com/lodging/1000000/10000/1500/1461/b5c018f9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Home2 Suites by Hilton East Haven New Haven The Centre $392 per person Apr 24 - Apr 26 found 20 hours ago Roundtrip flight included Atlanta (ATL) to New Haven (HVN) 9.6/10 Exceptional! (492 reviews) Be aware $150 for incidentals deposit Reviewed on Mar 10, 2026 ![Hampton Inn & Suites New Haven - South - West Haven](https://images.trvl-media.com/lodging/3000000/2080000/2078500/2078403/b6f421aa_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hampton Inn & Suites New Haven - South - West Haven $621 per person May 8 - May 10 found 24 hours ago Roundtrip flight included Atlanta (ATL) to New Haven (HVN) 8.4/10 Very Good! (1,002 reviews) Very friendly greeting at all times. Enjoyed our stay. Reviewed on Mar 8, 2026 ![Graduate by Hilton New Haven](https://images.trvl-media.com/lodging/38000000/37210000/37200100/37200005/d3190acf_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Graduate by Hilton New Haven Downtown New Haven $653 per person May 8 - May 10 found 24 hours ago Roundtrip flight included Atlanta (ATL) to New Haven (HVN) 9.2/10 Wonderful! (955 reviews) Groovy, fun, comfortable hotel in a great location. Reviewed on Mar 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/2026-04-12/2026-04-19/?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 4.5/5(13 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 $84 nightly $97 total Mar 30 - Mar 31 Total with taxes and fees 9/10 Wonderful! (2,027 reviews) The heater is set to never go above 74, if you use the thermostat to set it to 78 the fan goes on but the room never heats up. I had to sleep in pants and a sweater. All rooms are this way, booked here about 5 times because its the best location for me but at this point I'm fed up being cold. The ... Reviewed on Mar 12, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F30%2F2026&endDate=3%2F31%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 Fully refundableReserve now, pay when you stay $101 nightly $116 total Apr 5 - Apr 6 Total with taxes and fees 8.6/10 Excellent! (1,267 reviews) Nice and quiet place to stay Reviewed on Mar 10, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F5%2F2026&endDate=4%2F6%2F2026&selected=1562702&PinnedHotelID=1562702&HadPinnedHotel=true®ionId=183065) ![Cambria Hotel New Haven University Area](https://images.trvl-media.com/lodging/79000000/78620000/78614500/78614483/6990d1ac_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Cambria Hotel New Haven University Area 20 Dwight Street New Haven CT Fully refundable $119 nightly $137 total Mar 22 - Mar 23 Total with taxes and fees [](https://expedia.com/Hotel-Search?startDate=3%2F22%2F2026&endDate=3%2F23%2F2026&selected=78614483&PinnedHotelID=78614483&HadPinnedHotel=true®ionId=183065) [See all 1,056 properties in Middlebury](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F13%2F2026&endDate=3%2F14%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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Philadelphia (PHL) to Oxford (OXC) ](https://www.expedia.com/lp/flights/phl/oxc/philadelphia-to-oxford) - [Flights from Washington (IAD) to Oxford (OXC) ](https://www.expedia.com/lp/flights/iad/oxc/washington-to-oxford) - [Flights from Fresno (FAT) to Oxford (OXC) ](https://www.expedia.com/lp/flights/fat/oxc/fresno-to-oxford) - [Flights from Palm Springs (PSP) to Oxford (OXC) ](https://www.expedia.com/lp/flights/psp/oxc/palm-springs-to-oxford) - [Flights from Chicago (MDW) to Oxford (OXC) ](https://www.expedia.com/lp/flights/mdw/oxc/chicago-to-oxford) - [Flights from West Palm Beach (PBI) to Oxford (OXC) ](https://www.expedia.com/lp/flights/pbi/oxc/west-palm-beach-to-oxford) - [Flights from Columbus (CMH) to Oxford (OXC) ](https://www.expedia.com/lp/flights/cmh/oxc/columbus-to-oxford) - [Flights from Grand Rapids (GRR) to Oxford (OXC) ](https://www.expedia.com/lp/flights/grr/oxc/grand-rapids-to-oxford) - [Flights from Tri-Cities (TRI) to Oxford (OXC) ](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 (OXC) ](https://www.expedia.com/lp/flights/elm/oxc/elmira-to-oxford) - [Flights from Fargo (FAR) to Oxford (OXC) ](https://www.expedia.com/lp/flights/far/oxc/fargo-to-oxford) - [Flights from Beijing (PEK) to Oxford (OXC) ](https://www.expedia.com/lp/flights/pek/oxc/beijing-to-oxford) - [Flights from Wilmington (ILM) to Oxford (OXC) ](https://www.expedia.com/lp/flights/ilm/oxc/wilmington-to-oxford) - [Flights from San José (SJO) to Oxford (OXC) ](https://www.expedia.com/lp/flights/sjo/oxc/san-jose-to-oxford) - [Flights from Green Bay (GRB) to Oxford (OXC) ](https://www.expedia.com/lp/flights/grb/oxc/green-bay-to-oxford) - [Flights from Bismarck (BIS) to Oxford (OXC) ](https://www.expedia.com/lp/flights/bis/oxc/bismarck-to-oxford) - [Flights from Bangor (BGR) to Oxford (OXC) ](https://www.expedia.com/lp/flights/bgr/oxc/bangor-to-oxford) - [Flights from Burlington (BTV) to Oxford (OXC) ](https://www.expedia.com/lp/flights/btv/oxc/burlington-to-oxford) - [Flights from Albuquerque (ABQ) to Oxford (OXC) ](https://www.expedia.com/lp/flights/abq/oxc/albuquerque-to-oxford) - [Flights from Kansas City (MCI) to Oxford (OXC) ](https://www.expedia.com/lp/flights/mci/oxc/kansas-city-to-oxford) - [Flights from Orlando (SFB) to Oxford (OXC) ](https://www.expedia.com/lp/flights/sfb/oxc/orlando-to-oxford) - [Flights from Daytona Beach (DAB) to Oxford (OXC) ](https://www.expedia.com/lp/flights/dab/oxc/daytona-beach-to-oxford) - [Flights from Oaxaca Intl. (OAX) to Oxford (OXC) ](https://www.expedia.com/lp/flights/oax/oxc/oaxaca-intl-to-oxford) - [Flights from Las Vegas (LAS) to Oxford (OXC) ](https://www.expedia.com/lp/flights/las/oxc/las-vegas-to-oxford) - [Flights from San Juan (SJU) to Oxford (OXC) ](https://www.expedia.com/lp/flights/sju/oxc/san-juan-to-oxford) - [Flights from Chicago (CHI) to Oxford (OXC) ](https://www.expedia.com/lp/flights/chi/oxc/chicago-to-oxford) - [Flights from Norwood (OWD) to Oxford (OXC) ](https://www.expedia.com/lp/flights/owd/oxc/norwood-to-oxford) - [Flights from Blantyre (BLZ) to Oxford (OXC) ](https://www.expedia.com/lp/flights/blz/oxc/blantyre-to-oxford) - [Flights from Doha (DOH) to Oxford (OXC) ](https://www.expedia.com/lp/flights/doh/oxc/doha-to-oxford) - [Flights from Georgetown (GED) to Oxford (OXC) ](https://www.expedia.com/lp/flights/ged/oxc/georgetown-to-oxford) - [Quassy Amusement Park ](https://www.expedia.com/Quassy-Amusement-Park-Middlebury.d6089847.Vacation-Attraction) - [Hop Brook Lake ](https://www.expedia.com/Hop-Brook-Lake-Waterbury.d553248621561886346.Vacation-Attraction) - [Car rental Oxford Airport (OXC) ](https://www.expedia.com/Car-Rentals-In-Waterbury-Oxford.d6030940.Car-Rental-Guide) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.