Middlebury Vacations from $423
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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.
HYATT house Hartford North/Windsor
Save 100% on your flight
per person
Sep 12 - Sep 15
found 9 hours ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
9/10 Wonderful! (1,004 reviews)
Very easy navigation to the hotel. Got exactly the room that I reserved, and even a little bit better. The hotel staff from front desk agent to assistant general manager to bartender to the breakfast hostess Were all incredibly friendly and warm and responsive. It felt like staying at a friend's place. Their last act upon our checkout was reflective of the service throughout our Multi-day stay: I asked if the breakfast coffee was still out and the front desk agent told me it was not but then offered to get me a cup of coffee from the kitchen, which she did right away and with a smile. It was so nice and such a kind gesture to this weary traveler, and it's the little things like that that make this a great place to stay.
Reviewed on Jul 10, 2025
Omni New Haven Hotel at Yale
Downtown New Haven
Save 100% on your flight
per person
Aug 21 - Aug 24
found 15 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to New Haven (HVN)
8.4/10 Very Good! (1,015 reviews)
Clean room, friendly staff.
We stayed Sat-Mon and while the hotel was great, there was quite a bit of noise from the bars & partiers on the street. There was a panel under our window that let in all the sound. If I didn't have my earplugs, sleep would have been a struggle.
Not being used to the downtown environment, we didn't feel very safe in the area and chose to drive most of the time when leaving the hotel.
The restaurant on the 19th floor was great for our Monday breakfast with a varied menu and well-presented and delicious food.
Reviewed on Jul 12, 2025
Discover the most popular places to visit in Middlebury
Quassy Amusement Park
4.5/5(13 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
$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! (1,647 reviews)
"Very clean and spacious rooms"
Reviewed on Jul 12, 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 20 to Jul 21
$110 total
Jul 20 - Jul 21
Total includes taxes and fees
7.8/10 Good! (1,188 reviews)
Nice hotel terrible service from staff
"Room was great. Pool was clean. Breakfast was nice. The staff during the day was very rude primarily this one lady who was working pretty much every day shift. She wasn’t friendly and she didn’t want to be any help when I asked her if I could get any video footage of the parking lot so I could possibly ..."
Reviewed on Jul 12, 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 20 to Jul 21
$123 total
Jul 20 - Jul 21
Total includes taxes and fees
5.8/10 (1,023 reviews)
"The place was quiet and near to local shops"
Reviewed on Jul 3, 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.