Middlebury Vacations from $499
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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
Price was $884, price is now $711 per person
$711
per person
Dec 30 - Jan 6
found 24 hours ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
8.8/10 Excellent! (1,018 reviews)
Clean rooms, a bit outdated and showing signs of wear. Sunrise was gorgeous from my balcony. Food and drinks at the restaurant are quality. Staff was incredibly friendly and helpful, especially Chris at the front desk. I would stay here again.
Reviewed on Nov 7, 2025
Graduate by Hilton New Haven
Downtown New Haven
Price was $602, price is now $547 per person
$547
per person
Jan 2 - Jan 4
found 21 hours ago
Roundtrip flight included
Miami (MIA) to New Haven (HVN)
9.2/10 Wonderful! (889 reviews)
Very happy with my stay here! The staff was super friendly, the coffee shop on property had the most deeeelicious latte that I had throughout my entire trip! Love how the whole property is decorated as well. Very charming!
Reviewed on Nov 6, 2025
HYATT house Hartford North/Windsor
Price was $663, price is now $608 per person
$608
per person
Dec 30 - Jan 6
found 24 hours ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
9/10 Wonderful! (1,008 reviews)
Easy check-in, everyone at the desk was very friendly and helpful. The room was clean and comfortable.
Reviewed on Nov 2, 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
Holiday Inn Express Southington by IHG
120 Laning St, Southington, CT
Fully refundable
$83 nightly
The price is $95 total per night from Nov 16 to Nov 17
$95 total
Nov 16 - Nov 17
Total with taxes and fees
8.6/10 Excellent! (1,144 reviews)
The staff was very nice and professional. The room though, toilet seat was loose, door stopper was hanging off the wall, and the mattresses were EXTREMELY soft. The breakfast was very good though.
Reviewed on Nov 3, 2025
New Haven Hotel
229 George Street, New Haven, CT
Fully refundableReserve now, pay when you stay
$97 nightly
The price is $112 total per night from Dec 1 to Dec 2
$112 total
Dec 1 - Dec 2
Total with taxes and fees
9/10 Wonderful! (1,867 reviews)
It was spectacular!
Reviewed on Nov 4, 2025
Wyndham Southbury
1284 Strongtown Road, Southbury, CT
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $107 total per night from Nov 16 to Nov 17
$107 total
Nov 16 - Nov 17
Total with taxes and fees
8/10 Very Good! (1,005 reviews)
Staff at the desk were very helpful and nice.
Reviewed on Nov 6, 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.