Middlebury Vacations from $1,348
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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.
Luxury Furnished Apartments by Hyatus Downtown at Yale
The Hill
Save 100% on your flight
Price was $1,842, price is now $1,348 per person
$1,348
per person
Jun 25 - Jul 2
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) to New Haven (HVN)
9.6/10 Exceptional! (67 reviews)
The rooms are spacious and clean, kitchen is fully equipped for those who want to cook.
Reviewed on Mar 29, 2026
Hyatus Luxury Residences City Crossing
The Hill
Save 100% on your flight
Price was $2,340, price is now $1,708 per person
$1,708
per person
May 12 - May 17
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.2/10 Wonderful! (30 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
$126 nightly
The price is $145 total per night from Apr 16 to Apr 17
$145 total
Apr 16 - Apr 17
Total with taxes and fees
9.2/10 Wonderful! (2,076 reviews)
comfortable beds, clean rooms and general areas, helpful staff, very close to Yale University
Reviewed on Apr 8, 2026
Holiday Inn Express Southington by IHG
120 Laning St Southington CT
Fully refundable
$108 nightly
The price is $124 total per night from Apr 19 to Apr 20
$124 total
Apr 19 - Apr 20
Total with taxes and fees
8.6/10 Excellent! (1,263 reviews)
Clean lobby and great hotel staff. Hall way carpets could use a clean
Reviewed on Apr 8, 2026
Hyatt Place Milford / New Haven
190 Old Gate Lane Milford CT
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $122 total per night from Apr 19 to Apr 20
$122 total
Apr 19 - Apr 20
Total with taxes and fees
8.6/10 Excellent! (1,291 reviews)
The breakfast is excellent. A lot of choices. The room is spacious and clean. The staff are nice.
Reviewed on Apr 6, 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.
