Middlebury Vacations from $376
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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
Price was $489, price is now $376 per person
$376
per person
Sep 11 - Sep 13
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
9.2/10 Wonderful! (2,148 reviews)
Always feel back home when I see the smiles of the front desk staffs. Great location, convenient to everything! Clean rooms with decent space for travelers like me.
Reviewed on Jun 16, 2026
Pier Blue Inn Old Saybrook - Essex
Saybrook Manor
Price was $880, price is now $645 per person
$645
per person
Aug 8 - Aug 14
found 6 hours ago
Roundtrip non-stop flight included
Miami (MIA) to New Haven (HVN)
8/10 Very Good! (1,006 reviews)
It was in a good location and less expensive than area hotels.
Reviewed on Jun 15, 2026
Hyatus Luxury Residences City Crossing
The Hill
Price was $636, price is now $499 per person
$499
per person
Sep 11 - Sep 13
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
9.2/10 Wonderful! (31 reviews)
Great stay with many amenities to enjoy within the building!
Reviewed on Apr 3, 2026
Discover the most popular places to visit in Middlebury
Quassy Amusement Park
4.5/5(15 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.
Middlebury Hotel Deals
New Haven Hotel
229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $127 total per night from Jun 29 to Jun 30
$127 total
Jun 29 - Jun 30
Total with taxes and fees
9.2/10 Wonderful! (2,196 reviews)
"Always feel back home when I see the smiles of the front desk staffs. Great location, convenient to everything! Clean rooms with decent space for travelers like me."
Reviewed on Jun 16, 2026
Omni New Haven Hotel at Yale
155 Temple St New Haven CT
Fully refundableReserve now, pay when you stay
$149 nightly
The price is $172 total per night from Jul 6 to Jul 7
$172 total
Jul 6 - Jul 7
Total with taxes and fees
8.6/10 Excellent! (1,027 reviews)
"I would 100% stay here again. Prefect location only blocks away from Yale University. Convenient and walkable to lost of attractions. The staff was extraordinarily helpful. The hotel has a nice restaurant and bar on the 19th floor with a beautiful view of Yale Campus. Some reviews stated the decor ..."
Reviewed on Jun 10, 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 17 to Jun 18
$119 total
Jun 17 - Jun 18
Total with taxes and fees
8/10 Very Good! (1,662 reviews)
"Clean, helpful staff, decent breakfast. Only reason I didnt give 5 stars was due to traffic noise as it's next to the I-95"
Reviewed on Jun 14, 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.
