Middlebury Vacations from $497
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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.
Cambria Hotel New Haven University Area
West River
Save 100% on your flight
Price was $642, price is now $497 per person
$497
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8.8/10 Excellent! (869 reviews)
No issues! Clean, convenient & friendly staff. 15-20 walk to bars and restaurants
Reviewed on Sep 1, 2025
Graduate by Hilton New Haven
Downtown New Haven
Save 100% on your flight
Price was $1,149, price is now $852 per person
$852
per person
Oct 9 - Oct 14
found 20 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.2/10 Wonderful! (865 reviews)
Really close to Yale. No on site parking so we had to search for parking and walk back to the hotel late at night after we arrived…and there were some iffy characters around the area. More iffy characters greeted us near our parked car at 8:30am the next morning. The best part was Kristina at the front desk! She was really friendly and helpful.
Reviewed on Aug 31, 2025
Omni New Haven Hotel at Yale
Downtown New Haven
Save 100% on your flight
Price was $1,335, price is now $1,010 per person
$1,010
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8.4/10 Very Good! (1,010 reviews)
Staff was very friendly
Reviewed on Aug 31, 2025
Luxury Apartments by Hyatus at Pierpont
The Hill
Save 100% on your flight
Price was $782, price is now $597 per person
$597
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.4/10 Exceptional! (19 reviews)
Excellent location downtown and close to yale. A lot of complimentary amenities and activities. Very nice size rooms. A nice residential feel for a weeks stay.
Reviewed on Jun 27, 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
Trumbull Marriott Shelton
180 Hawley Ln, Trumbull, CT
Fully refundableReserve now, pay when you stay
$156 nightly
The price is $179 total per night from Sep 14 to Sep 15
$179 total
Sep 14 - Sep 15
Total with taxes and fees
Omni New Haven Hotel at Yale
155 Temple St, New Haven, CT
$143 nightly
The price is $165 total per night from Sep 21 to Sep 22
$165 total
Sep 21 - Sep 22
Total with taxes and fees
Holiday Inn Express Southington by IHG
120 Laning St, Southington, CT
Fully refundable
$113 nightly
The price is $130 total per night from Sep 25 to Sep 26
$130 total
Sep 25 - Sep 26
Total with taxes and fees
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.
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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.