Middlebury Vacations from $353
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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.
Sleep Inn & Suites Niantic
Price was $415, price is now $353 per person
$353
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New Haven (HVN)
8.4/10 Very Good! (1,008 reviews)
Small breakfast area lacked enough seating but otherwise a great stop near the casino.
Reviewed on Oct 15, 2025
Madison Beach Hotel
Madison Center
Save 100% on your flight
Price was $976, price is now $759 per person
$759
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New Haven (HVN)
9.4/10 Exceptional! (316 reviews)
Beautiful beach property that gives you such a feeling of luxury all around you. Staff has been great, very clean hallways and entire property. Balcony is beautiful!
Reviewed on Oct 14, 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
Trumbull Marriott Shelton
180 Hawley Ln, Trumbull, CT
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $160 total per night from Oct 26 to Oct 27
$160 total
Oct 26 - Oct 27
Total with taxes and fees
8/10 Very Good! (1,003 reviews)
"Nice facility overall. A few minor issues in the room that were quickly corrected."
Reviewed on Oct 16, 2025
Omni New Haven Hotel at Yale
155 Temple St, New Haven, CT
Fully refundableReserve now, pay when you stay
$167 nightly
The price is $192 total per night from Oct 30 to Oct 31
$192 total
Oct 30 - Oct 31
Total with taxes and fees
8.4/10 Very Good! (1,011 reviews)
"Friendly staff, very clean and the bed was great. We had the king deluxe room. I’ve never stayed in a big fancy hotel like that before so it was a little overwhelming but I got through it. Would stay there again if I ever came back to the area."
Reviewed on Oct 11, 2025
New Haven Hotel
229 George Street, New Haven, CT
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $137 total per night from Oct 26 to Oct 27
$137 total
Oct 26 - Oct 27
Total with taxes and fees
9/10 Wonderful! (1,834 reviews)
"The hotel was very nice. The room was clean and the staff was very friendly."
Reviewed on Oct 13, 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.
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.
