Middlebury Vacations from $467
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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.
New Haven Hotel
Downtown New Haven
Save 100% on your flight
Price was $1,006, price is now $728 per person
$728
per person
Aug 25 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
9.2/10 Wonderful! (2,140 reviews)
The property is centrally located to Yale, Toads for concerts, is close to highway and train station. Great restaurants within a short walk. One recommendation would be a locked entry from the parking garage as there is direct access to the hotel room floors. The garage is also gated, but the added layer would have made me feel more secure. Overall, great stay and I’d definitely come back!
Reviewed on Jun 8, 2026
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.
Middlebury Hotel Deals
New Haven Hotel
229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
$132 nightly
The price is $152 total per night from Jun 14 to Jun 15
$152 total
Jun 14 - Jun 15
Total with taxes and fees
9.2/10 Wonderful! (2,168 reviews)
"The property is centrally located to Yale, Toads for concerts, is close to highway and train station. Great restaurants within a short walk. One recommendation would be a locked entry from the parking garage as there is direct access to the hotel room floors. The garage is also gated, but the added ..."
Reviewed on Jun 8, 2026
Omni New Haven Hotel at Yale
155 Temple St New Haven CT
Fully refundableReserve now, pay when you stay
$142 nightly
The price is $163 total per night from Jul 2 to Jul 3
$163 total
Jul 2 - Jul 3
Total with taxes and fees
8.6/10 Excellent! (1,023 reviews)
"Very nice place, conveniently situated to Yale."
Reviewed on Jun 3, 2026
Best Western Executive Hotel Of New Haven - West Haven
490 Saw Mill Rd West Haven CT
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $119 total per night from Jun 10 to Jun 11
$119 total
Jun 10 - Jun 11
Total with taxes and fees
8/10 Very Good! (1,648 reviews)
"I was satisfied with all the above no complaints... Will be returning soon"
Reviewed on Jun 8, 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 |
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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.
