Middlebury Vacations from $414
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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, Palace Theatre and Brass Mill Center. 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.
Water's Edge Resort & Spa
Westbrook Center
$629
per person
Dec 10 - Dec 13
found 13 hours ago
Roundtrip flight included
Nashville (BNA) to New Haven (HVN)
8.8/10 Excellent! (1,004 reviews)
Beautiful property.The staff were very accommodating ,helpful and friendly.The only complaint to report was the lack of on site eating facilities .We arrived on a rainy Sunday and the outside venue for lunch was closed.The bar did not serve food until 3:30.The only option was the Sunday buffet which was priced at $59.00pp.Starbucks was limited to a grilled cheese or a ham egg sandwich.We were forced to leave the property to have lunch . The espresso martini was priced at &20.00 a tad high .Overall it was an enjoyable stay.
Reviewed on Sep 22, 2026
Head of Pond House
$658
per person
Dec 10 - Dec 13
found 13 hours ago
Roundtrip flight included
Nashville (BNA) to New Haven (HVN)
10/10 Exceptional! (13 reviews)
Excellent European B&B experience not often found in the States. A quaint well-managed property with hidden charm. The bedrooms were spacious , comfortable and
nicely designed with taste and simplicity.
Reviewed on Sep 20, 2026
Hyatus Luxury Residences City Crossing
The Hill
$604
per person
Dec 3 - Dec 6
found 16 hours ago
Roundtrip flight included
Nashville (BNA) to New Haven (HVN)
9.4/10 Exceptional! (34 reviews)
The room was spacious and clean. Close to new haven union station, yale university and downtown. We enjoyed the pool, gym and the rooftop. Check in and check out process were very smooth. Sarah was very responsive to our questions. Would def stay here again.
Reviewed on Aug 10, 2026
Stay near popular Middlebury attractions
Quassy Amusement Park
8.2/10 (21 reviews)
This century-old Connecticut park balances nostalgia with modern thrills, featuring the award-winning Wooden Warrior coaster and lakeside beach. Rent a waterpark cabana for a premium experience during hot summer days.
Middlebury Hotel Deals
New Haven Hotel
229 George Street New Haven CT
$123 nightly
$141 total
Sep 27 - Sep 28
Total with taxes and fees
Holiday Inn Express Southington by IHG
120 Laning St Southington CT
Fully refundableReserve now, pay when you stay
$92 nightly
$106 total
Sep 27 - Sep 28
Total with taxes and fees
Best Western Executive Hotel Of New Haven - West Haven
490 Saw Mill Rd West Haven CT
$110 nightly
$126 total
Oct 7 - Oct 8
Total with taxes and fees
8.2/10 Very Good! (1,858 reviews)
"The room had hairs on the toilet and in the sink. The toilet was not flushing down and the shower was not draining so it filled up as we took a shower. The staff at night was goofing off behind the counter with several women flirting with a young man sitting there. We will not stay here again."
Reviewed on Sep 21, 2026
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, Palace Theatre and Mount Southington Ski Area |
More vacations you might like
Frequently asked questions
How much does a Middlebury vacation package cost?
You can grab a vacation package to this top destination from $414 on Expedia. However, how much your vacation to Middlebury costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Middlebury?
You're likely to find lower prices and better availability in December, January and February. Take a look at our cheap Middlebury vacation packages and you could get some excellent off-season deals.
How many days is enough for Middlebury?
With a well-planned schedule, you can easily visit the most popular Middlebury sights in a handful of days. But if you want to venture off the beaten track or take day trips, consider booking your Middlebury vacation for longer.
How to find the best Middlebury package deals?
Landing a cheap Middlebury package deal is a breeze with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your maximum budget, add some filters and see what's available. You can tweak your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Middlebury package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Middlebury vacation as a package?
You can enjoy significant savings on your next Middlebury getaway by booking a customized vacation package. Click on the "Package" heading, then select your destination and travel dates to view the best flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Middlebury?
If you have your Middlebury vacation dates finalized, book as early as you can to score some terrific deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous trips? Our last-minute deals are great for jetting off on a whim.
Does Expedia offer Book Now, Pay Later Middlebury vacation packages?
If you're anything like us, you love jet-setting around the world but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the overall cost of your Middlebury vacation across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure great vacation packages with payment plans as soon as you spot them.
Explore a world of travel with Expedia
- Milford Hotels
- Norwalk Hotels
- Watertown Hotels
- Motels in Waterbury
- Romantic Hotels in Connecticut
- Resorts & Hotels with Spas in Connecticut
- Waterbury Hotels
- New Haven Hotels
- Pet-Friendly Hotels in Connecticut
- Hotels with an Indoor Pool in Connecticut
- Hotels near Mohegan Sun Casino
- Beach Hotels in Connecticut
- Hotels with Waterslides in Connecticut
- Bristol Hotels
- Southbury Hotels
- Shelton Hotels
- Hartford Hotels
- Extended Stay Hotels in Connecticut
- Luxury Hotels in Connecticut
- Connecticut Hotels
- Casino Hotels in Connecticut
- Stamford Hotels
- Cabin Rentals in Connecticut
- Hotels near Yale University
- Cheap Hotels in Connecticut
- Naugatuck Hotels
- Adults Only Resorts & in Connecticut
- Bridgeport Hotels
- Hamden Hotels
- Hotels with Hot Tubs in Connecticut
- Middlebury Hotels
- Danbury Hotels
- Family Hotels in Connecticut
- Wallingford Hotels
- Southington Hotels
- Oceanfront Hotels in Connecticut
- All-Inclusive Resorts in Connecticut
- Motels in Connecticut
- Flights from Bradley Intl.
- Flights from Los Angeles (LAX) to Hartford (BDL)
- Flights to New Haven
- Flights from Tweed - New Haven Regional
- Flights from Dallas (DFW) to Hartford (BDL)
- Flights from Hartford
- Flights to Hartford
- Flights from Danbury Municipal
- Flights from Connecticut
- Flights to Waterbury
- Flights from Chicago (ORD) to Hartford (BDL)
- Flights from Tampa (TPA) to Hartford (BDL)
- Flights from Orlando (MCO) to Hartford (BDL)
- Flights from Waterbury - Oxford
- Flights from Atlanta (ATL) to Hartford (BDL)
- Flights to Connecticut
- Flights to Bradley Intl.
- Flights from Charlotte (CLT) to Hartford (BDL)
- Yale University
- Visit Middlebury
- Waterbury Vacations
- Visit Connecticut
- Bellamy-Ferriday House and Garden
- Cheshire Hollow Farm
- Hope Memorial Field
- Southford Falls State Park
- Matthies Memorial Park
- Bethlehem Vacations
- Waterbury Green
- Abbey of Regina Laudis
- Apothecary Building
- Quassy Amusement Park
- Hop Brook Lake
- Prospect Vacations
- Harrub Pilgrim Memorial
- Union Station Clocktower
- Carrie Welton Fountain
- Pilgrim Mall Shopping Center
- Roxbury Vacations
- Holy Land USA
- Woodbury Vacations
- Visit New Haven
- Brass Mill Center
- Peterson Park
- Sandy Hook Vacations
- Connecticut Vacations
- Morris Vacations
- Sterling Memorial Library at Yale University
- Little Art Shop
- Flanders Nature Center
- Old Bethlehem Historical Society Museum
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
