Middlebury Vacations from $170
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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.
Residence Inn by Marriott Southington
Save 100% on your flight
Price was $746, price is now $499 per person
$499
per person
Feb 14 - Feb 21
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
8.6/10 Excellent! (581 reviews)
Room was clean, staff was super friendly. Only problem was the nozzle on the bath tub it was dripping the entire stay
Reviewed on Nov 30, 2025
Graduate by Hilton New Haven
Downtown New Haven
Save 100% on your flight
Price was $281, price is now $202 per person
$202
per person
Jan 8 - Jan 10
found 23 hours ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
9.2/10 Wonderful! (908 reviews)
Nice throwback hotel. Room was spotless, much old school charm. Check in was a little bumpy, otherwise a good stay.
Reviewed on Nov 17, 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
$80 nightly
The price is $92 total per night from Dec 25 to Dec 26
$92 total
Dec 25 - Dec 26
Total with taxes and fees
9/10 Wonderful! (1,907 reviews)
Convenient location for visiting Yale. The hotel lobby area is nice for spending time outside of room when travelling with a family oe friends.
Reviewed on Nov 29, 2025
Cambria Hotel New Haven University Area
20 Dwight Street New Haven CT
Fully refundable
$111 nightly
The price is $128 total per night from Dec 23 to Dec 24
$128 total
Dec 23 - Dec 24
Total with taxes and fees
8.6/10 Excellent! (981 reviews)
They didn't give us the room type we booked on Expedia for our first night. After much back and forth, they made us shift into the right room type on our second day at the property. Guests had to sleep on sofa beds for the first night, hotel blamed this on Expedia not communicating properly with ...
Reviewed on Nov 25, 2025
Holiday Inn Express Southington by IHG
120 Laning St Southington CT
Fully refundable
$91 nightly
The price is $105 total per night from Dec 20 to Dec 21
$105 total
Dec 20 - Dec 21
Total with taxes and fees
8.6/10 Excellent! (1,157 reviews)
The rooms are nice and the staff is accommodating. The fitness center could use an upgrade
Reviewed on Nov 22, 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.
