Middlebury Vacations from $377
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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.
Hilton Garden Inn Hartford North/Bradley Int'l Airport
per person
Sep 30 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to New Haven (HVN)
8.8/10 Excellent! (1,002 reviews)
Our experience was great, from check in to check out the staff was great! We checked in and found an issue with our room that was quickly resolved with little hesitation by the staff; we were moved to a different room and we realized we left our food in the original room at midnight and without hesitation the staff helped us. At check out three hours later, we were greeted by the same staff members with smiles and wished us a safe trip and rest of our travels. It was everything you expect from a stay at a Hilton hotel. If management reads this, they should use this location to train other hotels in the same way. I will definitely stay at this location and encourage others to stay. Can’t give the staff any more accolades without sounding biased. Thank you for such a positive experience for me and my daughter even if it was a short stay.
Reviewed on Jul 16, 2025
Holiday Inn Express Southington by IHG
per person
Sep 3 - Sep 7
found 7 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to New Haven (HVN)
8.8/10 Excellent! (1,023 reviews)
The rooms are small, but that was ok. Great location for our softball tournament. Close to the interstate.
Reviewed on Jul 18, 2025
Omni New Haven Hotel at Yale
Downtown New Haven
per person
Aug 29 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to New Haven (HVN)
8.4/10 Very Good! (1,015 reviews)
This was a very nice place to stay for a fair price. The breakfast buffet was very expensive with understaffed service
Reviewed on Jul 15, 2025
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
$144 nightly
The price is $165 total per night from Jul 28 to Jul 29
$165 total
Jul 28 - Jul 29
Total includes taxes and fees
8.8/10 Excellent! (1,646 reviews)
"Our stay at this hotel was wonderful! We were greeted by an amazing front desk staff who was very kind and helpful. Would recommend this hotel to anyone!"
Reviewed on Jul 16, 2025
Best Western Executive Hotel Of New Haven - West Haven
490 Saw Mill Rd, West Haven, CT
Fully refundableReserve now, pay when you stay
$96 nightly
The price is $110 total per night from Jul 27 to Jul 28
$110 total
Jul 27 - Jul 28
Total includes taxes and fees
7.8/10 Good! (1,208 reviews)
"First room smelled like cigarettes"
Reviewed on Jul 18, 2025
La Quinta Inn & Suites by Wyndham New Haven
400 Sargent Dr, New Haven, CT
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $123 total per night from Jul 28 to Jul 29
$123 total
Jul 28 - Jul 29
Total includes taxes and fees
5.8/10 (1,032 reviews)
Pleasant stay
"Very grateful for my time here"
Reviewed on Jul 18, 2025
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.