Middlebury Vacations from $642
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, 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.
Luxury Furnished Apartments by Hyatus Downtown at Yale
The Hill
$642
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip flight included
Indianapolis (IND) to New Haven (HVN)
9.6/10 Exceptional! (88 reviews)
Excellent value — a very thoughtfully decorated and well-maintained apartment, effective air conditioning, blackout curtains in every room — really helped the vacation to feel like a “treat”!
I did feel their app / web portal had “quite a lot” baked in it which could feel intimidating at first — vs. a “easy button” version at the top for simple functions like lock/unlock door — but would absolutely consider other Hyatus properties in the future!
Reviewed on Sep 18, 2026
Hyatus Luxury Residences City Crossing
The Hill
$915
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
Tampa (TPA) 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
Landing Apartments New Haven Near Dixwell
Newhallville
$1,036
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
2/10 (1 review)
The parking situation is very unclear. There is a small sign far from the lot that warns of towing but nothing in the area where you park. No significant warnings in communications with host.
Reviewed on May 25, 2026
Landing Furnished Apartment Near Yale University
Downtown New Haven
$875
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
2/10 (2 reviews)
Check in automated, but the key box was broken and it took me 30 on the phone with IT to get the keys. When I entered the apartment a water leak in the city had destroyed a chunk of the ceiling and there was a mess of drywall and dirty water on the floor. The firm tried to relocate me an hour away before promising to clean up and repair the problem while I was out, but maintenance never arrived. We had to book a hotel nearby. These people are incompetent
Reviewed on Sep 14, 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
Fully refundableReserve now, pay when you stay
$129 nightly
$148 total
Oct 27 - Oct 28
Total with taxes and fees
Trumbull Marriott Shelton
180 Hawley Ln Trumbull CT
$152 nightly
$175 total
Oct 18 - Oct 19
Total with taxes and fees
Best Western Executive Hotel Of New Haven - West Haven
490 Saw Mill Rd West Haven CT
Fully refundableReserve now, pay when you stay
$110 nightly
$126 total
Oct 11 - Oct 12
Total with taxes and fees
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 |
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Frequently asked questions
How much does a Middlebury vacation package cost?
You can grab a vacation package to this top destination from $642 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.
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- Yale University
- Visit Middlebury
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- Visit Connecticut
- Bellamy-Ferriday House and Garden
- Cheshire Hollow Farm
- Hope Memorial Field
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- Abbey of Regina Laudis
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- Little Art Shop
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.